1-(4-Azidobutyl)cyclopentanecarboxylic acid → 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(4-azidobutyl)cyclopentyl]-carbonyl]-L-phenylalanine methyl ester

HRID 393461Notes

Reaction equation

HRID 393461 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]1([C:13]([OH:15])=O)[CH2:12][CH2:11][CH2:10][CH2:9]1)=[N+:2]=[N-:3].Cl.[CH3:17][O:18][C:19](=[O:40])[C@H:20]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][C:30]([C:32]2[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:39])=[O:31])=[CH:25][CH:24]=1)[NH2:21]>>[CH3:17][O:18][C:19](=[O:40])[C@H:20]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([C:32]2[C:37]([Cl:38])=[CH:36][CH:35]=[CH:34][C:33]=2[Cl:39])=[O:31])=[CH:27][CH:28]=1)[NH:21][C:13]([C:8]1([CH2:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[CH2:9][CH2:10][CH2:11][CH2:12]1)=[O:15]

Participants

3

Reactant 2

HCID 226601411-(4-Azidobutyl)cyclopentanecarboxylic acidHCID 23383932methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochloride

Product 1

HCID 590725614-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(4-azidobutyl)cyclopentyl]-carbonyl]-L-phenylalanine methyl ester

Procedure

4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[I-(4-azidobutyl)cyclopentyl]-carbonyl]-L-phenylalanine methyl ester was prepared from 1-[4-(azido)butyl]cyclopentane carboxylic acid and of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine methyl ester hydrochloride salt using the procedure described in example 46 to give a 99% yield of a white solid, mp 195-199° C. HR MS (C27H31Cl2N5O4): Obs mass, 560.1833. Calcd mass, 560.1831 (M+H).

Sources & evidence

ORD record
ord-101f6205f79f4662a5b72b93611e08e3
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

Loading…