17701-61-0|Benzyl 3-hydroxy-2,2-dimethylpropanoate| Ambeed

Structure of 17701-61-0

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Quality Control of [ 17701-61-0 ] Purity: 97% SDS Specification

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Product Details of [ 17701-61-0 ]

CAS No. :	17701-61-0
Formula :	C₁₂H₁₆O₃
M.W :	208.25
SMILES Code :	O=C(OCC1=CC=CC=C1)C(C)(C)CO
MDL No. :	MFCD09951815
Boiling Point :	No data available
InChI Key :	PLZZXRKTRWITII-UHFFFAOYSA-N
Pubchem ID :	18922595

Safety of [ 17701-61-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 17701-61-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	6
Fraction Csp3	0.42
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	57.63
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	46.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.31
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.79
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.6
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.98
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.98

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.22
Solubility	1.24 mg/ml ; 0.00596 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.39
Solubility	0.857 mg/ml ; 0.00411 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.15
Solubility	0.147 mg/ml ; 0.000708 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.3 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.77

Application In Synthesis of [ 17701-61-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 17701-61-0 ]
Downstream synthetic route of [ 17701-61-0 ]

[ 17701-61-0 ] Synthesis Path-Upstream 1~7

1
[ 4835-90-9 ]
[ 100-39-0 ]
[ 17701-61-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 16 h;	Reference Example 1 Benzyl 3-hydroxy-2,2-dimethylpropanoate [0391] [0392] 2,2-Dimethyl-3-hydroxypropanoic acid (10.0 g) was dissolved in N,N-dimethylformamide (150 mL). To this solution, potassium hydrogen carbonate (10.2 g) was added, and then, benzyl bromide (10.7 mL) was added thereto. The resulting solution was stirred at room temperature for 16 hours. To the reaction mixture, water (300 mL) was added, and extraction was performed with a mixed solution of n-hexane and ethyl acetate (1:4) (200 mL×2). The organic layers were combined and washed with a saturated aqueous solution of sodium chloride (200 mL), and then dried over magnesium sulfate. After magnesium sulfate was removed by filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (a medium-pressure preparative liquid chromatograph, W-prep 2XY manufactured by Yamazen Corporation (column: main column 4L, inject column 3L, n-hexane:ethyl acetate=1:0-1:1 (gradient time: 15 minutes), fractionation mode GR), whereby the title compound (17.6 g, 100percent) having the following physical properties was obtained. [0393] TLC (Rf value): 0.39 (n-hexane:ethyl acetate=3:1) [0394] NMR (CDCl₃): δ 7.29-7.41 (m, 5H), 5.15 (s, 2H), 3.57 (d, J=6.3 Hz, 2H), 1.22 (s, 6H)
3.04 g	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 5 h;	LiOH (15.9 g, 37.9 mmol) in THF/MeOH/H₂O (1:1:0.5, 62.5 mL) was added to a solution of 3-hydroxy-2,2-dimethylpropionate 14 (5 g, 37.9 mmol) in THF/MeOH (1:1, 25 mL) at 0 °C. The solution was warmed to rt and stirred for 1.5 h, the reaction mixture was adjusted to pH 2 by addition of H₂SO₄. The solution was concentrated under reduced pressure to remove THF and the residue washed with H₂O (10 mL), extracted with EtOAc (3 12 mL), dried over Na₂SO₄ and concentrated under reduced pressure to give the acid (3.3 g, 27.9 mmol, 73percent) as a white solid. Benzyl bromide (1.9 mL, 16.1 mmol) was added to a solution of crude acid (2.0 g, 16.9 mmol) and K₂CO₃ (2.57 g, 18.6 mmol) in DMF (20 mL). The reaction mixture was stirred for 5 h then quenched by the addition of H₂O (5 mL). The reaction mixture was extracted with Et₂O (3 10 mL). The combined organic extracts were washed with brine (10 mL), dried over Na₂SO₄ and concentrated under reduced pressure. Purification by column chromatography using 9:1 to 3:2 hexanes/EtOAc as eluent gave the title compound 20 (3.04 g, 86percent) as a yellow oil. R_f: 0.48 (60percent hexanes/EtOAc); δ_H (400 MHz, CDCl₃): 7.39-7.29 (5H, m, Ph), 5.14 (2H, s, CH₂Ph), 3.57 (2H, d, J = 6.4 Hz, H-3), 2.54 (1H, br s, OH), 1.21 (6H, s, 2 CH₃); δ_C (100 MHz, CDCl₃): 176.9 (C=O, C-1), 135.8 (C, Ph), 128.3 (2 CH, Ph), 127.9 (CH, Ph), 127.5 (2 CH, Ph), 69.3 (CH₂, C-3), 66.1 (CH₂, CH₂Ph), 44.2 (C, C-2), 21.8 (2 CH₃). The spectroscopic data were in agreement with those reported in the literature.⁷

References: [1] Patent: US2013/245074, 2013, A1, . Location in patent: Paragraph 0391-0394.
[2] Journal of the American Chemical Society, 2002, vol. 124, # 34, p. 9966 - 9967.
[3] Patent: EP1544208, 2005, A1, . Location in patent: Page/Page column 43.
[4] Patent: EP1452526, 2004, A1, . Location in patent: Page 55.
[5] Tetrahedron, 2014, vol. 70, # 3, p. 590 - 596.
[6] Patent: WO2017/96301, 2017, A1, . Location in patent: Page/Page column 165.

2
[ 100-39-0 ]
[ 17701-61-0 ]

References: [1] Patent: WO2007/53346, 2007, A1, . Location in patent: Page/Page column 13.

3
[ 21620-60-0 ]
[ 100-39-0 ]
[ 17701-61-0 ]

References: [1] Patent: WO2007/53394, 2007, A1, . Location in patent: Page/Page column 23-24.

4
[ 100-39-0 ]
[ 17701-61-0 ]

References: [1] Patent: WO2006/17443, 2006, A2, . Location in patent: Page/Page column 92-93.

5
[ 14002-80-3 ]
[ 17701-61-0 ]

References: [1] Journal of the American Chemical Society, 2002, vol. 124, # 34, p. 9966 - 9967.
[2] Tetrahedron, 2014, vol. 70, # 3, p. 590 - 596.

6
[ 1301764-12-4 ]
[ 100-39-0 ]
[ 17701-61-0 ]

References: [1] Patent: US5512589, 1996, A, .

7
[ 4835-90-9 ]
[ 7285-83-8 ]
[ 17701-61-0 ]

References: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 36, p. 7997 - 8002.

[ 17701-61-0 ] Synthesis Path-Downstream 1~35

1
[ 524-38-9 ]
[ 17701-61-0 ]
[ 464189-15-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 1h;	[91] A solution of diisopropylazodicarboxylate (DIAD, 0.52 mL, 2.8 mmol) prepared in 2 mL anhydrous THF) was slowly added to a stirred mixture of benzyl 3-hydroxy-2,2- dimethylpropanoate (590 mg, 2.8 mmol), triphenylphosphine (820 mg, 3.1 mmol) and N- hydroxyphthalimide (510 mg, 3.1 mmol) prepared in 20 mL anhydrous THF at 0 C. After stirring the mixture at room temperature under a nitrogen atmosphere for 24 h, THF was removed under reduced pressure and the residue re-dissolved in 40 mL of ethyl acetate. The ethyl acetate mixture was washed with water (10 mL) three times, brine and dry-loaded onto a 40-g silica column. The final product was obtained in 73% yield (730 mg) as a white solid after FCC purification (hexane/ethyl acetate). [92] NMR (CDCh, 400 MHz): 5 7.84 (m, 2H), 7.76 (s, 2H), 7.39 (m, 5H), 5.19 (s, 2H), 4.32 (s, 2H), 1.42 (s, 6H); 13C NMR (CDC13, 100 MHz): 5 175.0, 163.1, 136.0, 134.4, 129.0, 128.5, 128.1, 123.5, 83.6, 66.7, 43.2, 22.2, MS (ESI+): m/z (intensity), 354.4 ([M+H]+, 100%).

References: [1]Patent: WO2018/144880,2018,A1 .Location in patent: Paragraph 23; 91-92.
[2]Journal of the American Chemical Society,2002,vol. 124,p. 9966 - 9967.

2
[ 4835-90-9 ]
[ 100-39-0 ]
[ 17701-61-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20℃; for 16h;	Reference Example 1 Benzyl 3-hydroxy-2,2-dimethylpropanoate [0391] [0392] 2,2-Dimethyl-3-hydroxypropanoic acid (10.0 g) was dissolved in N,N-dimethylformamide (150 mL). To this solution, potassium hydrogen carbonate (10.2 g) was added, and then, benzyl bromide (10.7 mL) was added thereto. The resulting solution was stirred at room temperature for 16 hours. To the reaction mixture, water (300 mL) was added, and extraction was performed with a mixed solution of n-hexane and ethyl acetate (1:4) (200 mL×2). The organic layers were combined and washed with a saturated aqueous solution of sodium chloride (200 mL), and then dried over magnesium sulfate. After magnesium sulfate was removed by filtration, the solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (a medium-pressure preparative liquid chromatograph, W-prep 2XY manufactured by Yamazen Corporation (column: main column 4L, inject column 3L, n-hexane:ethyl acetate=1:0-1:1 (gradient time: 15 minutes), fractionation mode GR), whereby the title compound (17.6 g, 100%) having the following physical properties was obtained. [0393] TLC (Rf value): 0.39 (n-hexane:ethyl acetate=3:1) [0394] NMR (CDCl3): delta 7.29-7.41 (m, 5H), 5.15 (s, 2H), 3.57 (d, J=6.3 Hz, 2H), 1.22 (s, 6H)
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 5h;	To a suspension of hydroxypivalic acid (3 g) and potassium carbonate (3.9 g) in N,N-dimethylformamide (25 mL) was added benzyl bromide (2.9 mL), and the mixture was stirred at room temperature for 5 hours. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The organic layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give the title compound (4.7 g).1H-NMR (CDCl3) delta ppm: 1.22 (6H, s), 2.33 (1H, t, J=6.7Hz), 3.58 (2H, d, J=6.7Hz), 5.15 (2H, s), 7.3-7.4 (5H, m)
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 20℃; for 12h;	Hydroxypivalic acid (5.03 g) was dissolved in DMF (50 ml) and benzyl bromide (5.50 ml) and potassium carbonate (11.38 g) were successively added. The mixture was stirred at room temperature for 12 hr. Water (100 ml) was added to the reaction mixture and the mixture was extracted with ether (2×100 ml). The organic layer was washed successively with water (2×50 ml) and saturated aqueous sodium chloride solution (50 ml), dried and concentrated under reduced pressure. The obtained oily substance was purified by column chromatography to give the title compound (6.54 g) as a colorless oil.1H-NMR(delta, 300MHz, CDCl3) 1.22(6H,s),2.37(1H,t,J=6.8Hz),3.58(2H,d,J=6.8Hz),5.15(2H,s),7. 30-7.40(5H,m).

3.04 g	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 5h;	LiOH (15.9 g, 37.9 mmol) in THF/MeOH/H2O (1:1:0.5, 62.5 mL) was added to a solution of 3-hydroxy-2,2-dimethylpropionate 14 (5 g, 37.9 mmol) in THF/MeOH (1:1, 25 mL) at 0 C. The solution was warmed to rt and stirred for 1.5 h, the reaction mixture was adjusted to pH 2 by addition of H2SO4. The solution was concentrated under reduced pressure to remove THF and the residue washed with H2O (10 mL), extracted with EtOAc (3 12 mL), dried over Na2SO4 and concentrated under reduced pressure to give the acid (3.3 g, 27.9 mmol, 73%) as a white solid. Benzyl bromide (1.9 mL, 16.1 mmol) was added to a solution of crude acid (2.0 g, 16.9 mmol) and K2CO3 (2.57 g, 18.6 mmol) in DMF (20 mL). The reaction mixture was stirred for 5 h then quenched by the addition of H2O (5 mL). The reaction mixture was extracted with Et2O (3 10 mL). The combined organic extracts were washed with brine (10 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography using 9:1 to 3:2 hexanes/EtOAc as eluent gave the title compound 20 (3.04 g, 86%) as a yellow oil. Rf: 0.48 (60% hexanes/EtOAc); deltaH (400 MHz, CDCl3): 7.39-7.29 (5H, m, Ph), 5.14 (2H, s, CH2Ph), 3.57 (2H, d, J = 6.4 Hz, H-3), 2.54 (1H, br s, OH), 1.21 (6H, s, 2 CH3); deltaC (100 MHz, CDCl3): 176.9 (C=O, C-1), 135.8 (C, Ph), 128.3 (2 CH, Ph), 127.9 (CH, Ph), 127.5 (2 CH, Ph), 69.3 (CH2, C-3), 66.1 (CH2, CH2Ph), 44.2 (C, C-2), 21.8 (2 CH3). The spectroscopic data were in agreement with those reported in the literature.7
		Take compound XIII-1 (12.403 g, 105 mmol) and dissolve it in N, N-dimethylformamide (124 mL, 0.805 M).Potassium carbonate (15.894 g, 115 mmol) was added sequentially,Benzyl bromide (11.877mL, 100mmol),The temperature was raised to 70 C.After 3.5 hours of reaction,TLC monitors the end of the reaction.Most of N, N-dimethylformamide was distilled off under reduced pressure,Add water (300mL),Ethyl acetate (50mL x 5) extraction,Combined organic phases,Washed with saturated saline (100mL x 2),Dry over anhydrous sodium sulfate.The solvent was distilled off under reduced pressure,The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 20/1),A colorless oil was obtained. The obtained oil was dissolved in anhydrous tetrahydrofuran (150 mL),Triphenylphosphine (39.342 g, 150 mmol) was added sequentially,Pyridine (3.955 mL, 114 mmol).Under nitrogen protection and ice bath conditions,A solution of carbon tetrabromide (38.137 g, 115 mmol) in tetrahydrofuran (50 mL) was added dropwise.React overnight,TLC monitors the end of the reaction.Add n-hexane (50 mL),There is solid precipitation,Suction filtration,The filter cake was washed with tetrahydrofuran (5 mL x 2),The filtrate was concentrated,The residue was purified by column chromatography (eluent: petroleum ether / ethyl acetate = 300/1),Compound XIII-2 was obtained (yellow oil, 4.659 g, yield 17%).

References: [1]Patent: US2013/245074,2013,A1 .Location in patent: Paragraph 0391-0394.
[2]Journal of the American Chemical Society,2002,vol. 124,p. 9966 - 9967.
[3]Patent: EP1544208,2005,A1 .Location in patent: Page/Page column 43.
[4]Patent: EP1452526,2004,A1 .Location in patent: Page 55.
[5]Tetrahedron,2014,vol. 70,p. 590 - 596.
[6]Patent: WO2017/96301,2017,A1 .Location in patent: Page/Page column 165.
[7]Patent: CN110372638,2019,A .Location in patent: Paragraph 0642; 0644; 0645.

3
[ 14002-80-3 ]
[ 17701-61-0 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 9966 - 9967.
[2]Tetrahedron,2014,vol. 70,p. 590 - 596.

4
[ 17701-61-0 ]
3-aminooxy-N-isobutyl-2,2-dimethyl-propionamide [ No CAS ]