2-Methyl-5-nitrobenzoic acid → N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[[(2-methyl-5-nitrophenyl)carbonyl]amino]-L-phenylalanine

HRID 393428Notes

Reaction equation

HRID 393428 reaction equation
C[O:2][C:3](=[O:30])[C@H:4]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[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].[CH3:31][C:32]1[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:33]=1[C:34](O)=[O:35]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][C:8]2([C:6]([NH:5][C@H:4]([C:3]([OH:2])=[O:30])[CH2:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:34]([C:33]4[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:32]=4[CH3:31])=[O:35])=[CH:25][CH:24]=3)=[O:7])[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 5196832-Methyl-5-nitrobenzoic acidHCID 544852054-Amino-N-[[1[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 10196565N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[[(2-methyl-5-nitrophenyl)carbonyl]amino]-L-phenylalanineYield 72.1%

Procedure

4-Amino-N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-L-phenylalanine methyl ester (23.4 mg, 0.057 mmol) and 2-methyl-5-nitrobenzoic acid 13 mg, 0.07 mmol) were reacted as described in example 40 to give 23 mg (69%) of N-[[1-[(4-methoxyphenyl)methyl]cyclopentyl]carbonyl]-4-[[(2-methyl-5-nitrophenyl)carbonyl]amino]-L-phenylalanine, HR—FAB—MS: obs. mass 560.2413. Calcd. mass 560.2397 (M+H).

Sources & evidence

ORD record
ord-c958310edd7c43bfa56db4bb5505e5f9
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

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