71510-95-7|Ethyl 3-(methylamino)-3-oxopropanoate| Ambeed

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Quality Control of [ 71510-95-7 ] Purity: 96% SDS Specification

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Product Details of [ 71510-95-7 ]

CAS No. :	71510-95-7
Formula :	C₆H₁₁NO₃
M.W :	145.16
SMILES Code :	O=C(OCC)CC(NC)=O
MDL No. :	MFCD08458724
InChI Key :	VWTRXRCWWIJCCQ-UHFFFAOYSA-N
Pubchem ID :	11321015

Safety of [ 71510-95-7 ]

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

Computational Chemistry of [ 71510-95-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.67
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	35.24
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	55.4 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.08
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	-0.07
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.31
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.	-0.16
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	0.06
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.12

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.37
Solubility	62.5 mg/ml ; 0.431 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.	-0.64
Solubility	33.1 mg/ml ; 0.228 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	-1.13
Solubility	10.7 mg/ml ; 0.074 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.	-7.24 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	1.0
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	1.0 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)	1.34

Application In Synthesis of [ 71510-95-7 ]

* 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 [ 71510-95-7 ]

[ 71510-95-7 ] Synthesis Path-Downstream 1~35

1
[ 36239-09-5 ]
[ 74-89-5 ]
[ 71510-95-7 ]

References: [1]Journal of Organic Chemistry,1962,vol. 27,p. 2160 - 2162.

2
[ 74-89-5 ]
[ 105-53-3 ]
[ 71510-95-7 ]

References: [1]Farmaco, Edizione Scientifica,1979,vol. 34,p. 595 - 611.

3
[ 71510-95-7 ]
[ 95-54-5 ]
[ 91598-13-9 ]

References: [1]Farmaco, Edizione Scientifica,1984,vol. 39,p. 477 - 486.

5
[ 19172-47-5 ]
[ 156025-63-7 ]
C₁₃H₁₈NO₆PS [ No CAS ]
[ 71510-95-7 ]
[ 56409-14-4 ]
[ 858128-33-3 ]

References: [1]Heteroatom Chemistry,2006,vol. 17,p. 676 - 684.

6
[ 71510-95-7 ]
[ 323203-14-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	In isopropyl alcohol; mineral oil;	EXAMPLE 26 Preparation of the Amide of Formula (III) in Which R is Methyl and R1 is Isopropyl 1.4 g sodium hydride (60% in mineral oil) are added to a solution prepared by dissolving 101.5 g of <strong>[71510-95-7]2-carboethoxy-N-methyl-acetamide</strong> in 11 of isopropanol. The reaction is maintained at room temperature for 5 hours. The mixture is neutralised with acetic acid, then the solvent is removed at reduced pressure, and the product is isolated by distillation at 6 mmHg (Teb 115 C.). 91.4 g of 2-carboisopropoxy-N-methyl-acetamide are obtained (yield 82%).
82%	In isopropyl alcohol; mineral oil;	EXAMPLE 26 Preparation of the amide of formula (III) in which R is methyl and R1is isopropyl 1.4 g sodium hydride (60% in mineral oil) are added to a solution prepared by dissolving 101.5 g of <strong>[71510-95-7]2-carboethoxy-N-methyl-acetamide</strong> in 1 l of isopropanol. The reaction is maintained at room temperature for 5 hours. The mixture is neutralised with acetic acid, then the solvent is removed at reduced pressure, and the product is isolated by distillation at 6 mmHg (Teb115C). 91.4 g of 2-carboisopropoxy-N-methyl-acetamide are obtained (yield 82%).

References: [1]Patent: US6444822,2002,B1 .
[2]Patent: EP1074550,2001,A1 .

7
[ 71510-95-7 ]
[ 459-57-4 ]
[ 202534-94-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate; acetic acid; In water; ethyl acetate;	EXAMPLE 4 (+-)-trans-3-Ethoxycarbonyl-4-(4'-fluorophenyl)-N-methylpiperidin-2,6-dione (E4) A solution of p-fluorobenzaldehyde (100 g) in ethyl acetate (100 ml) was added slowly to a mixture of sodium methoxide (105 g) in ethyl acetate (900 ml), maintaining the temperature at 10-20 C. and stirring for a further 30 minutes at 15-25 C. Then a solution of desiccated ethyl N-methylamidomalonate (139 g) in ethyl acetate (200 ml) was added over 1 hour whilst maintaining the temperature at 15-25 C. and stirring for a further 1-2 hours. The resulting mixture was added to a solution of acetic acid (120 g) in water (475 ml) and stirred for 15 minutes. The lower aqueous layer was then separated and discarded. The rich solvent was washed with saturated brine (250 ml). The solvent was removed by vacuum distillation and replaced with propan-2-ol then cooled with stirring to obtain the crystalline title compound. Water (600 ml) was added over 30 minutes and the mixture stirred for 1-2 hours at 15-25 C. The product was filtered and washed with water then isopropyl ether before drying.
	With sodium methylate; acetic acid; In water; ethyl acetate;	Example 4 (+-)-trans-3-Ethoxycarbonyl-4-(4'-fluorophenyl)-N-methyl-piperidin-2,6-dione (E4) A solution of p-fluorobenzaldehyde (100g) in ethyl acetate (100ml) was added slowly to a mixture of sodium methoxide (105g) in ethyl acetate (900ml), maintaining the temperature at 10-20C and stirring for a further 30 minutes at 15-25C. Then a solution of desiccated ethyl N-methylamidomalonate (139g) in ethyl acetate (200ml) was added over 1 hour whilst maintaining the temperature at 15-25C and stirring for a further 1-2 hours. The resulting mixture was added to solution of acetic acid (120g) in water (475ml) and stirred for 15 minutes. The lower aqueous layer was then separated and discarded. The rich solvent was washed with saturated brine (250ml). The solvent was removed by vacuum distillation and replaced with propan-2-ol then cooled with stirring to obtain the crystalline title compound. Water (600ml) was added over 30 minutes and the mixture stirred for 1-2 hours at 15-25C. The product was filtered and washed with water then isopropyl ether before drying. Yield = 80-90%

References: [1]Patent: US4902801,1990,A .
[2]Patent: EP223334,1991,B1 .

8
[ 71510-95-7 ]
[ 104-55-2 ]
C₁₅H₁₉NO₄ [ No CAS ]
[ 323203-12-9 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 1943 - 1946.

9
[ 71510-95-7 ]
3-[3-(4-fluorophenyl)acryloyl]-(R)-4-phenyl-oxazolidin-2-one [ No CAS ]
[ 188302-25-2 ]

Yield	Reaction Conditions	Operation in experiment
80%		To a stired solution of <strong>[71510-95-7]ethyl-N-methylmalonamide</strong> 5 (4.84 g, 33.34 mmol) in dimethylsulfoxide (40.0 mL) was added sodium hydride (60%, 1.8 g, 45.0 mmol) slowly under nitrogen. The reaction mixture was cooled to room temperature, compound 4 added (10.0 g, 32.12 mmol) in a single portion and the whole mixture was stirred for 3-4 h at room temperature. The mixture was neutralized with acetic acid (4.0 mL) and extracted with ethyl acetate (2 × 25 mL) and the combined organic portions were washed with water (30.0 mL) and brine (30.0 mL). The solvent was removed under reduced pressure and the residue was diluted with diisopropyl ether (80.0 mL). The separated undissolved solid (phenyl oxazolidinone) was filtered and the mother liquor was evaporated and the residue recrystalized from heptane to afford 6 (7.5 g, 80%) as an off white solid. inlMMLBox (c 1, ethanol); IR (cm-1): 2965, 1746, 1725, 1671, 1311, 1109; 1H NMR: (400 MHz, CDCl3) delta, ppm: 7.16-7.20 (m, 2H), 7.01-7.05 (m, 2H), 4.07-4.12 (q, J = 8 Hz, 2H), 3.63-3.77 (m, 2H), 3.20 (s, 3H), 2.98-3.03 (dd, J = 9.3 Hz, 1H), 2.76-2.84 (dd, J = 9.3 Hz, 1H) , 1.08-1.11 (t, J = 8 Hz, 3H); 13C NMR (400 MHz, CDCl3): delta 170.5, 168.7, 167.6, 163.6, 134.4, 128.6, 116.3, 116.1, 62.0, 56.5, 39.0, 37.8, 27.0, 14.0; MS: m/z: 313.7 [M+H+].

References: [1]Tetrahedron Asymmetry,2011,vol. 22,p. 1 - 3.

10
[ 14371-10-9 ]
[ 71510-95-7 ]
(3R,4S,6S)-ethyl 6-hydroxy-1-methyl-2-oxo-4-phenylpiperidine-3-carboxylate [ No CAS ]