192214-06-5|(R)-1-Cbz-Pyrrolidine-3-carboxylic acid| Ambeed

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Quality Control of [ 192214-06-5 ] Purity: 97% SDS Specification

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Product Details of [ 192214-06-5 ]

CAS No. :	192214-06-5
Formula :	C₁₃H₁₅NO₄
M.W :	249.26
SMILES Code :	O=C([C@H]1CN(C(OCC2=CC=CC=C2)=O)CC1)O
MDL No. :	MFCD08692037
InChI Key :	JSASVUTVTRNJHA-LLVKDONJSA-N
Pubchem ID :	25418128

Safety of [ 192214-06-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 192214-06-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	6
Fraction Csp3	0.38
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	68.39
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.	2.02
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	1.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.2
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.	1.31
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	1.03
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.37

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.11
Solubility	1.94 mg/ml ; 0.00779 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.	-2.28
Solubility	1.3 mg/ml ; 0.00521 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	-2.08
Solubility	2.05 mg/ml ; 0.00822 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.	-6.91 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)	2.69

Application In Synthesis of [ 192214-06-5 ]

* 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 [ 192214-06-5 ]

[ 192214-06-5 ] Synthesis Path-Downstream 1~35

1
[ 192214-06-5 ]
[ 74-88-4 ]
(R)-methyl-1-benzyloxycarbonyl-pyrrolidine-3-carboxylate [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

2
[ 192214-06-5 ]
[ 72580-54-2 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778.

3
[ 329012-80-8 ]
[ 192214-06-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778.

4
[ 192214-05-4 ]
[ 192214-06-5 ]

Yield	Reaction Conditions	Operation in experiment
79%	With Jones reagent; In acetone; at 20.0℃; for 0.5h;	Step-3: Preparation of (R)- 1 -Benzyloxycarbonyl-pyrrolidine-3-carboxylic acid (X):To a solution of (R)-(1-benzyloxycarbonyl-pyrrolidin-3-yl)-methanol (IX, 80 gm, 0.34 mol) dissolved in acetone (800 ml) was added drop-wise under stirring Jones? reagent (200 ml, prepared by dissolving 53.4 gm Cr03 in a solution prepared by mixing 46 ml H2S04 and 140 ml water and fmal volume adjusted to 200 ml) at 20C tifi dark red colour persists of a solution and green coloured solid separates. The suspension was stirred for next 30 minutes. As the TLC (10% methanol in chloroform) showed complete conversion, isopropyl alcohol (100 ml) was added drop-wise to the reaction mixture, tifi green colour persists for 10 minutes. The suspension was filtered on the celite bed under suction and the solids were washed with fresh acetone (100 ml twice). The filtrate was evaporated under vacuum and to the residue was added saturated aqueous sodium bicarbonate solution (600 ml) tifi pH 8. The resultant mixture was extracted with ethyl acetate (400 ml) and layers were separated. Aqueous layer was adjusted to pH 2 by using 6N aqueous hydrochloric acid (125 ml). The reaction mixture was extracted with ethyl acetate (500 ml x 2) and dried over sodium sulfate. Evaporation of solvent afforded (R)- 1 -benzyloxycarbonyl-pyrrolidine-3-carboxylic acid (X) in 67 gm quantity as an oily syrup in 79% yield.Analysis:NMR: (CDC13):9.25 (br s, 1H), 7.25-7.35 (m, 5H), 5.13 (s, 2H), 3.62-3.71 (m, 2H), 3.52-3.54 (m, 1H), 3.43-3.49 (m, 1H), 3.07-3.10 (m, 1H), 2.09-2.18 (m, 2H).Mass (M-1): 248.1 for C13H15N04.

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.
[2]Patent: WO2014/135932,2014,A1 .Location in patent: Page/Page column 12; 13.

5
[ 85701-08-2 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

6
[ 501-53-1 ]
(+-)-2.3-diamino-propionic acid [ No CAS ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778.

7
[ 5082-74-6 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

8
[ 172796-28-0 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

9
[ 192214-02-1 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

10
[ 192214-01-0 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

11
[ 192214-03-2 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

12
[ 192214-04-3 ]
[ 192214-06-5 ]

References: [1]Journal of Organic Chemistry,1997,vol. 62,p. 5215 - 5218.

13
[ 100858-32-0 ]
[ 192214-06-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778.

14
[ 158654-83-2 ]
[ 192214-06-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1773 - 1778.

15
[ 192214-06-5 ]
(R)-2-Pyrrolidin-3-yl-propan-2-ol [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

16
[ 192214-06-5 ]
(S)-1-crotonoyl-2-(1-hydroxy-1-methylethyl)pyrrolidine [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

17
[ 192214-06-5 ]
(S)-1-cinnamoyl-2-(1-hydroxy-1-methylethyl)pyrrolidine [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

18
[ 192214-06-5 ]
(R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3,7-dimethyl-oct-6-en-1-one [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

19
[ 192214-06-5 ]
(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

20
[ 192214-06-5 ]
(R)-1-[(R)-3-(1-Hydroxy-1-methyl-ethyl)-pyrrolidin-1-yl]-3-phenyl-heptan-1-one [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 1909 - 1914.

21
[ 188846-99-3 ]
[ 192214-06-5 ]
[ 192214-00-9 ]
[ 329012-80-8 ]
[ 193693-69-5 ]