Acetamidomalonic acid diethyl ester → N-acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline ethyl ester

HRID 496240

Reaction equation

HRID 496240 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH:7]=[CH:8][CH:9]=O)=[CH:5][CH:4]=1.[C:13]([NH:16][CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:15])[CH3:14]>>[C:13]([N:16]1[CH2:9][CH2:8][CH:7]([C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:17]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 14041Acetamidomalonic acid diethyl esterHCID 2309953-(4-Methoxyphenyl)prop-2-enal

Product 1

HCID 10021599N-acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline ethyl esterYield 79.5%

Procedure

N-Acetyl-2-ethoxycarbonyl-3-(4-methoxyphenyl)proline, ethyl ester (13 g, 72%) was prepared from 4-methoxycinnamaldehyde (Lancaster, 8.1 g, 50 mmol) and diethyl acetamidomalonate (Aldrich, 9.9 g, 45 mmol) by the procedure described by Chung et al (J. Org. Chem. 1990, 55, 270).

Sources & evidence

ORD record
ord-29f119994b164dc189e90a8054097d9b
Source dataset
uspto-grants-2005_09
Patent number
US06943180B2

Linked notes

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