188528-95-2|1-tert-Butyl 3-ethyl 2-oxopyrrolidine-1,3-dicarboxylate| Ambeed

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Quality Control of [ 188528-95-2 ] Purity: 95% SDS Specification

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Product Details of [ 188528-95-2 ]

CAS No. :	188528-95-2
Formula :	C₁₂H₁₉NO₅
M.W :	257.28
SMILES Code :	O=C(N1C(C(C(OCC)=O)CC1)=O)OC(C)(C)C
MDL No. :	MFCD24466252
InChI Key :	OFHTXTVNVCVIBX-UHFFFAOYSA-N
Pubchem ID :	11207608

Safety of [ 188528-95-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 188528-95-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	18
Num. arom. heavy atoms	0
Fraction Csp3	0.75
Num. rotatable bonds	6
Num. H-bond acceptors	5.0
Num. H-bond donors	0.0
Molar Refractivity	67.69
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	72.91 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.55
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	1.45
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.95
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.	0.4
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	0.87
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.95
Solubility	2.87 mg/ml ; 0.0112 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.	-2.59
Solubility	0.666 mg/ml ; 0.00259 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	-1.37
Solubility	11.0 mg/ml ; 0.0428 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	No
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.	-6.84 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	2.0 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<0.0
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)	3.11

Application In Synthesis of [ 188528-95-2 ]

* 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 [ 188528-95-2 ]

[ 188528-95-2 ] Synthesis Path-Downstream 1~35

1
[ 400-91-9 ]
[ 188528-95-2 ]
3-(5-bromo-2,4-dinitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]
3-(5-bromo-2,4-dinitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3670 - 3671.

2
[ 70-34-8 ]
[ 188528-95-2 ]
3-(2,4-dinitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]
3-(2,4-dinitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3670 - 3671.
[2]Journal of Organic Chemistry,2006,vol. 71,p. 4980 - 4987.

3
[ 143879-77-0 ]
[ 188528-95-2 ]
3-(2-cyano-3-fluoro-4-nitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]
3-(2-cyano-3-fluoro-4-nitro-phenyl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3670 - 3671.

4
[ 696-82-2 ]
[ 188528-95-2 ]
3-(2,6-difluoro-pyrimidin-4-yl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]
3-(2,6-difluoro-pyrimidin-4-yl)-2-oxo-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3670 - 3671.

5
[ 70-34-8 ]
[ 188528-95-2 ]
6-amino-1H-spiro[indole-3,3'-pyrrolidine]-2,2'-dione [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 4980 - 4987.

6
[ 541-41-3 ]
[ 188528-95-2 ]

Yield	Reaction Conditions	Operation in experiment
67%		A THF solution (10 ml) that contained the crude product of 2-oxopyrrolidin-1-carboxylic acid tert-butyl (500 mg, 2.70 mmol) was added dropwise at -78C to a 1 M lithium hexamethyldisilazane THF solution (5.4 ml, 5.4 mmol), and the obtained mixture was stirred for 50 minutes. A solution obtained by dissolving ethyl chloroformate (0.27 ml, 2.84 mmol) in THF (5 ml) was further added dropwise to the reaction solution at -78C. The temperature of the mixture was increased to a room temperature, and the mixture was then stirred for 4 hours. Thereafter, the reaction solution was poured into a saturated ammonium chloride aqueous solution, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel chromatography (hexane : ethyl acetate = 5 : 1 to 2 : 1), so as to obtain 2-oxopyrrolidin-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (468 mg, 67%) in the form of a liver brown oil substance. 1H-NMR (270MHz, CDCl3) delta (ppm): 1.31 (3H, t, J=7.1Hz), 1.53 (9H, s), 2.16-2.46 (2H, m), 3.53 (1H, dd, J=7.4, 9.1Hz), 3.66-3.75 (1H, m), 3.84-3.93 (1H, m), 4.24 (2H, dd, J=7.1, 14.3Hz) ESI (LC-MS positive mode) m/z 258 (M+H).

References: [1]Patent: EP1854792,2007,A1 .Location in patent: Page/Page column 108.

7
[ 188528-95-2 ]
[ 36821-26-8 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 1h;	The <strong>[188528-95-2]2-oxopyrrolidin-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester</strong> (100 mg, 0.389 mmol) prepared in step A was suspended in dichloromethane (5 ml), and trifluoroacetic acid (0.5 mg, 6.490 mmol) was then added dropwise to the suspension under cooling on ice. The temperature of the mixture was increased to a room temperature, and the mixture was then stirred for 1 hour. Thereafter, the reaction solution was concentrated, so as to obtain a crude product of 2-oxopyrrolidin-3-carboxylic acid ethyl.
	With hydrogenchloride; In 1,4-dioxane; dichloromethane; at 15℃; for 1h;	To a solution of 1- (tert-butyl) 3-ethyl 2-oxopyrrolidine-1, 3-dicarboxylate (563.00 g, 2.19 mol) in DCM (200 mL) is added HCl/dioxane (4 M, 3.29 L) at 15 . The reaction mixture is stirred for 1 hour. The reaction mixture is concentrated under reduced pressure at 45 to give the title compound (381.00 g, 1.67 mol, 76.37) as a brown oil. The crude material is used without further purification.

References: [1]Patent: EP1854792,2007,A1 .Location in patent: Page/Page column 108-109.
[2]Patent: WO2017/5069,2017,A1 .Location in patent: Page/Page column 9; 140.

8
[ 188528-95-2 ]
6-amino-1H-spiro[indole-3,3'-pyrrolidine]-2,2'-dione [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 3670 - 3671.

9
[ 24424-99-5 ]
[ 188528-95-2 ]