204688-60-8|(R)-2-(1-Boc-3-pyrrolidinyl)acetic Acid| Ambeed

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Quality Control of [ 204688-60-8 ] Purity: 98% SDS Specification

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Product Details of [ 204688-60-8 ]

CAS No. :	204688-60-8
Formula :	C₁₁H₁₉NO₄
M.W :	229.27
SMILES Code :	O=C(O)C[C@@H]1CN(C(OC(C)(C)C)=O)CC1
MDL No. :	MFCD05861547
InChI Key :	SKEXQIJIXQSFRX-MRVPVSSYSA-N
Pubchem ID :	1502099

Safety of [ 204688-60-8 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H410
Precautionary Statements:	P273-P301+P310-P305+P351+P338
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Computational Chemistry of [ 204688-60-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	0
Fraction Csp3	0.82
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	63.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.84 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
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	1.0
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.34
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.	1.03
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	0.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.21

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.56
Solubility	6.29 mg/ml ; 0.0274 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.99
Solubility	2.33 mg/ml ; 0.0102 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.78
Solubility	38.0 mg/ml ; 0.166 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.	-6.99 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.	0.56

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)	2.59

Application In Synthesis of [ 204688-60-8 ]

* 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.

Downstream synthetic route of [ 204688-60-8 ]

[ 204688-60-8 ] Synthesis Path-Downstream 1~29

1
[ 24424-99-5 ]
[ 204688-60-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;	b) A solution of 4.95 g of the preceding step product in 50 ml of dichloromethane and 25 ml of trifluoroacetic acid is stirred at room temperature for 3 h. and concentrated. The residue is dissolved in 40 ml of dioxan and 40 ml of 1N NaOH, treated at room temperature with 4.3 g of di-tert-butyl dicarbonate in 40 ml of dioxan and stirred for 1.5 h. The reaction mixture is diluted with ether, the organic phase is washed with 1N NaOH and the aqueous phase is acidified with 3N HCl. Extraction of the aqueous phase with ether, washing, drying and concentration of the ether phase gives 0.72 g of tert-butyl(R)-3-carboxymethyl-pyrrolidine-1-carboxylate.

References: [1]Patent: US5726185,1998,A .

2
[ 67-56-1 ]
[ 204688-60-8 ]
[ 1024038-31-0 ]

Yield	Reaction Conditions	Operation in experiment
		(R)-methyl 2-(pyrrolidin-3-yl)acetate hydrochloride; <strong>[204688-60-8](R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid</strong> (5.0 g, 21.81 mmol) in 4N HCl in dioxane (50 mL) was stirred at ambient temperature for 20 hours. The mixture was evaporated, coevaporated with dioxane (3×30 mL) and dried under high vacuum to give a yellow oil.This was dissolved in methanol (50 mL) at 10 C. and the solution saturated with HCl gas. The reaction mixture was then allowed to warm to ambient temperature and evaporated. The residue was co-evaporated with methanol (2×30 mL) and toluene (3×30 mL) and dried under high vacuum to give a yellow oil (4.0 g).1H NMR (400.13 MHz, DMSO-d6) delta 1.52-1.57 (1H, m), 2.063-2.13 (1H, m), 2.47-2.59 (3H, am), 2.7-2.8 (1H, m), 3.03-3.12 (1H, m), 3.14-3.25 (1H, m), 3.27-3.48 (3H, m), 3.61 (3H, s), 9.42 (2H, s)

References: [1]Patent: US2008/269288,2008,A1 .Location in patent: Page/Page column 105.

3
[ 204688-60-8 ]
[ 765-30-0 ]
C₁₄H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; at 23℃; for 1h;	(R)-2-(1-(tert-Butoxycarbonyl)pyrrolidin-3-yl)acetic acid (500 mg, 2.18 mmol), HATU (995 mg, 2.62 mmol) and cyclopropylamine (0.181 mL, 2.62 mmol) were stirred in DMF (10 mL) at 23 C. for 1 h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with 5% aqueous KHSO4, saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The solvent was evaporated. The product was then dissolved in Hydrogen chloride (10.90 mL, 10.90 mmol) (1M/AcOH) and stirred at 23 C. for 3-4 h. The solvent was evaporated and the product was dried under vacuum overnight. The product was used directly for the next step. Yield: 400 mg (90%).

References: [1]Patent: US2009/62251,2009,A1 .Location in patent: Page/Page column 52.

4
[ 204688-60-8 ]
[ 1212182-03-0 ]

Yield	Reaction Conditions	Operation in experiment
100%		Borane-THF complex (3.90 kg or L of 1 M in THF, mol) was added slowly to a stirred solution of (R)-2-(1-(terf-butoxycarbonyl)pyrrolidine-3-yl)acetic acid (683 g, 3.03 mol) in THF (2.5 kg), kept under nitrogen gas, and using a water bath to keep the temperature between 23 and 28 C. The addition took 1.75 h. Stirring at 25 C was continued for 1 h, after which time GC analysis indicated complete reaction. The reaction mixture was cooled to <10 C and maintained below 25 C as 10% aqueous sodium hydroxide (1.22 kg) was slowly added. The addition took 40 min. The mixture was stirred 1 h at 25 C, and then combined with 1 :1 (v/v) heptane/ethyl acetate (7 L). The mixture was stirred for 15 min and allowed to separate into phases (1 h). The organic phase was withdrawn, and the aqueous phase was combined with a second 7 L portion of 1 :1 heptane/ethyl acetate. This was stirred for 15 min and allowed to separate into phases (20 min). The organic phase was again withdrawn, and the combined organic phases were washed with saturate aqueous sodium chloride (4.16 kg), using 15 min of mixing and 1 h of settling time. The organic phase was combined with silica gel (140 g) and stirred 1 h. The anhydrous sodium sulfate (700 g) was added, and the mixture was stirred for 1.5 h. The mixture was filtered, and the filter cake was washed with 1 :1 heptane/ethyl acetate (2 L). The filtrate was concentrated under vacuum at <40 C for 6 h. The resulting oil weighed 670 g (103% yield) and contains traces of heptane, but is otherwise identical to previously prepared samples of 6, by NMR analysis.
91.3%		Example 6. Synthesis of tert-butyl (R)-3-(2-hydroxyethyl)pyrrolidine-1-carboxylate (6); Procedure A; A solution of (R)-2-(1-(feAt-butoxycarbonyl)pyrroliotadiotane-3-yl)acetiotac acid (49 0 g, 214 mmol) in tetrahydrofuran (THF) (200 mL) was cooled to -10 0C 250 mL (250 mmol) of a 1 M borane in THF solution was added slowly to the flask while maintaining the temperature lower than 0 C The solution was warmed to ambient temperature and stirred for 1 h The solution was sampled hourly and analyzed by HPLC to establish completion of the reaction Upon completion of the reaction, the solution was cooled to 0 0C, and a 10% sodium hydroxide solution (80 mL) was added drop-wise over a 30 minute period to control gas evolution The solution was extracted with 500 mL of a 1 1 hexanes/ethyl acetate solution The organic layer was washed with saturated sodium chloride solution and dried with 10 g of silica gel The silica gel was removed by filtration and washed with 100 mL of 1 1 hexanes/ethyl acetate The organic layers were combined and concentrated under vacuum to give 6 (42 g, 91 3 %) as a light-orange oil that solidified upon sitting 1H NMR (CDCI3, 400 MHz) delta 3 67 (m, 2H), 3 38-3 62 (m, 2H), 3 25 (m, 1 H), 2 90 (m, 1 H), 2 25 (m, 1 H), 1 98-2 05 (m, 1 H) 1 61-1 69 (m, 2H), 1 48-1 59 (m, 2H), 1 46 (s, 9H)
91.3%		Example 6. Synthesis of tert-butyl (R)-3-(2-hydroxyethyl)pyrrolidine-1- carboxylate (6)Procedure A: A solution of (R)-2-(1-(terf-butoxycarbonyl)pyrrolidine-3- yl)acetic acid (49.0 g, 214 mmol) in tetrahydrofuran (THF) (200 mL) was cooled to - 10 0C. 250 mL (250 mmol) of a 1 M borane in THF solution was added slowly to the flask while maintaining the temperature lower than 0 0C. The solution was warmed to ambient temperature and stirred for 1 h. The solution was sampled hourly and analyzed by HPLC to establish completion of the reaction. Upon completion of the reaction, the solution was cooled to 0 0C, and a 10% sodium hydroxide solution (80 mL) was added drop-wise over a 30 minute period to control gas evolution. The solution was extracted with 500 mL of a 1 :1 hexanes/ethyl acetate solution. The organic layer was washed with saturated sodium chloride solution and dried with 10 g of silica gel. The silica gel was removed by filtration and washed with 100 mL of 1 :1 hexanes/ethyl acetate. The organic layers were combined and concentrated under vacuum to give 6 (42 g, 91.3 %) as a light-orange oil that solidified upon sitting. 1H NMR (CDCI3, 400 MHz) delta 3.67 (m, 2H), 3.38-3.62 (m, 2H), 3.25 (m, 1 H), 2.90 (m, 1 H), 2.25 (m, 1 H), 1.98-2.05 (m, 1 H), 1.61-1.69 (m, 2H), 1.48-1.59 (m, 2H), 1.46 (s, 9H).

References: [1]Patent: WO2011/112428,2011,A2 .Location in patent: Page/Page column 33.
[2]Patent: WO2010/65447,2010,A2 .Location in patent: Page/Page column 35.
[3]Patent: WO2010/65443,2010,A1 .Location in patent: Page/Page column 38.

5
[ 1228312-13-7 ]
[ 204688-60-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	In dimethyl sulfoxide; toluene; for 2h;Reflux;Product distribution / selectivity;	A suspension of (f?)-2-(1-(tert-butoxycarbonyl)pyrroliotadiotan-3-yl)maloniotac acid (15 g, 55 mmol) in toluene (150 mL) and dimethylsulfoxide (2 mL) was heated to reflux for a period of 2 h The mixture was allowed to reach ambient and diluted with MTBE (150 mL) The organic solution was washed with 10% aqueous citric acid (2 x 200 mL), and the solvent was removed under vacuum to afford 11 6 g of (R)-2-(1-(tert-butoxycarbonyl)-pyrrolidin-3-yl)acetic acid as an off- white solid (92% yield) 1H NMR (DMSOd6, 400 MHz) delta 12 1 (s, 1 H), 3 36-3 48 (m, 1 H), 3 20- 3 34 (m, 1 H), 3 05-3 19 (m, 1 H, 2 72-2 84 (m, 1 H), 2 30-2 42 (m, 1 H), 2 22-2 30 (m, 2H), 1 85-2 00 (m, 1 H), 1 38-1 54 (m, , 1 H), 1 35 (2, 9H)
92%	In dimethyl sulfoxide; toluene; for 2h;Reflux;Product distribution / selectivity;	A suspension of (R)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)malonic acid (15 g, 55 mmol) in toluene (150 ml.) and dimethylsulfoxide (2 mL) was heated to reflux for a period of 2 h. The mixture was allowed to reach ambient and diluted with MTBE (150 mL). The organic solution was washed with 10% aqueous citric acid (2 * 200 mL), and the solvent was removed under vacuum to afford 1 1.6 g of (ft)-2-(1-(tert- butoxycarbonyl)-pyrrolidin-3-yl)acetic acid as an off-white solid (92% yield). 1H NMR (DMSOd6, 400 MHz): delta 12.1 (s, 1 H); 3.36-3.48 (m, 1 H); 3.20-3.34 (m, 1 H); 3.05- 3.19 (m, 1 H; 2.72-2.84 (m, 1 H); 2.30-2.42 (m, 1 H), 2.22-2.30 (m, 2H); 1.85-2.00 (m, 1 H); 1.38-1.54 (m, , 1 H), 1.35 (2, 9H).
92%	With dimethyl sulfoxide; In toluene; for 2h;Reflux;Product distribution / selectivity;	A suspension of (f?)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)malonic acid (15 g, 55 mmol) in toluene (150 mL) and dimethylsulfoxide (2 mL) was heated to reflux for a period of 2 h. The mixture was allowed to reach ambient and diluted with MTBE (150 mL). The organic solution was washed with 10% aqueous citric acid (2 chi 200 mL), and the solvent was removed under vacuum to afford 11.6 g of (R)-2-(1-(tert-butoxycarbonyl)-pyrrolidin-3- yl)acetic acid as an off-white solid (92% yield). 1H NMR (DMSO-d6, 400 MHz): delta 12.1 (s, 1 H); 3.36-3.48 (m, 1 H); 3.20-3.34 (m, 1 H); 3.05-3.19 (m, 1 H; 2.72-2.84 (m, 1 H); 2.30-2.42 (m, 1 H), 2.22-2.30 (m, 2H); 1.85-2.00 (m, 1 H); 1.38-1.54 (m, , 1 H), 1.35 (2, 9H).

53%

With citric acid; In dimethyl sulfoxide; toluene; for 4h;Reflux;

2-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-yl)-malonic acid diethyl ester (0.785 g, 2.38 mmol) obtained in StepA was dissolved in 8 mL of THF. 6N NaOH (2 ml, 11.9 mmol) was added thereto, and the mixture was stirred at 40Cfor 16 hours. The reaction solution was adjusted to pH 2 by the use of 6N HCl aqueous solution and extracted withEtOAc. The organic layer was dried with anhydrous magnesiumsulfate and concentrated under reduced pressure toobtain 2-((R)-1-tert-butoxycarbonyl-pyrrolidin-3-yl)-malonic acid. The obtained compound was dissolved in 4.5 ml oftoluene. 0.06 ml of DMSO was added thereto, and the mixture was stirred for 4 hours under reflux. After addition of 10%citric acid, the reaction solution was extracted with EtOAc. The organic layer was dried with anhydrous magnesiumsulfateand purified by column chromatography to obtain the title compound (0.29 g, 53 %).1H-NMR (CDCl3) delta 3.62 (1H, m), 3.45 (1H, m), 3.29 (1H, m), 2.96 (1H, m), 2.56 (1H, m), 2.44 (2H, d), 2.07 (1H, m), 1.57(1H, m), 1.44 (9H, s).

References: [1]Patent: WO2010/65447,2010,A2 .Location in patent: Page/Page column 35.
[2]Patent: WO2010/65443,2010,A1 .Location in patent: Page/Page column 38.
[3]Patent: WO2011/112428,2011,A2 .Location in patent: Page/Page column 32.
[4]Patent: EP3239143,2017,A2 .Location in patent: Paragraph 0548.

6
[ 127423-61-4 ]
[ 204688-60-8 ]

References: [1]Patent: WO2011/112428,2011,A2 .
[2]Patent: WO2011/112428,2011,A2 .
[3]Patent: EP3239143,2017,A2 .

7
[ 204688-60-8 ]
[ 958026-61-4 ]

References: [1]Patent: WO2011/112428,2011,A2 .

8
[ 204688-60-8 ]
[ 1228312-14-8 ]

References: [1]Patent: WO2011/112428,2011,A2 .

9
[ 1228312-12-6 ]
[ 204688-60-8 ]

References: [1]Patent: WO2011/112428,2011,A2 .
[2]Patent: EP3239143,2017,A2 .

10
[ 204688-60-8 ]
[ 64-17-5 ]
1,1-dimethylethyl(3R)-3-[2-(ethyloxy)-2-oxoethyl]-1-pyrrolidinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In diethyl ether; at 20℃; for 40h;Inert atmosphere;	a) 1,1-dimethylethyl (3R)-3-[2-(ethyloxy)-2-oxoethyl]-l-pyrrolidinecarboxylateIn an oven-dried 250 mL round bottom flask under nitrogen, ((3R)-1-[(1,1- dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)acetic acid (2.181 mmol) dissolved in diethyl ether (5 mL) was treated with l-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (2.4 mmol), 4-(dimethylamino)pyridine (0.218 mmol), and ethanol (4.8 mmol) at room temperature and the mixture was stirred overnight. The resulting white gummy precipitate was diluted with ether (100 mL) and washed with 1M aq sodium hydrogen sulfate solution (100 mL), saturated aq sodium bicarbonate solution (100 mL), and brine (100 mL). The organic phase was isolated, dried over magnesium sulfate, and concentrated in vacuo to give the title compound as a clear oil (95%). MS(ES)+ m/e 258.1 [M+H]+, 280.0 [M+Na]+.

References: [1]Patent: WO2011/103546,2011,A1 .Location in patent: Page/Page column 163.

11
[ 204688-60-8 ]
[ 1332333-63-7 ]