N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester → 4-Amino-N-[[1[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester

HRID 393425Notes

Reaction equation

HRID 393425 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][CH:24]=1)[NH:5][C:6]([C:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]>C(O)C>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([NH2:29])=[CH:27][CH:28]=1)[NH:5][C:6]([C:8]1([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

3

Reactant 1

HCID 54278434N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester

Product 1

HCID 544852054-Amino-N-[[1[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl esterYield 95.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester (253 mg, 0.575 mmol) in 10 mL of ethanol was hydrogenated at atmospheric pressure over 45 mg of 10% Pd(C) for 3 hours. The reaction mixture was filtered through a pad of celite and evaporated to dryness to give 4-amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester (225 mg, 95%) as a white solid suitable for use in the next step, HR—FAB—MS: Obs mass, 410.2196. Calcd mass, 410.2200 (M+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-ee7d2b7effda42e2925da6f3b81353ae
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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