N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → N-[3-[(benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester

HRID 327520Notes

Reaction equation

HRID 327520 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22](=[O:47])[C@H:23]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH:24][C:25](=[O:39])[C@H:26]([CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[NH2:27])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[CH2:14]([O:21][C:22](=[O:47])[C@H:23]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[NH:24][C:25](=[O:39])[C@H:26]([CH2:28][C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])[NH:27][C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 10004433L-Asp(OBzl)-L-Phe-OBzl

Product 1

HCID 10371852N-[3-[(benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester

Procedure

N-(t-butoxycarbonyl)-β-alanine was coupled with N-[3-[(benzyloxy)-carbonyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester to give N-[3-[(benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-β-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester, m.p. 124°-125° C.

Sources & evidence

ORD record
ord-9971ad7a40bd45ee983506004220ecbb
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Reaction notes

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