N-[3-[(benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester → N-[3-[(benzyloxy)carbonyl]-N-[N-[(5-cyano-2-pyridyl)carbonyl]-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester

HRID 1647123Notes

Reaction equation

HRID 1647123 reaction equation
[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[NH:11][C:12](=[O:38])[C@H:13]([CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29])[NH:14][C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19](OC(C)(C)C)=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:47]([C:49]1[CH:50]=[CH:51][C:52](C(O)=O)=[N:53][CH:54]=1)#[N:48]>>[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH:11][C:12](=[O:38])[C@H:13]([CH2:27][C:28]([O:30][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:29])[NH:14][C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:19]([C:52]1[CH:51]=[CH:50][C:49]([C:47]#[N:48])=[CH:54][N:53]=1)=[O:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 10371852N-[3-[(benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl esterHCID 124007345-Cyanopyridine-2-carboxylic acid

Product 1

HCID 54354798N-[3-[(benzyloxy)carbonyl]-N-[N-[(5-cyano-2-pyridyl)carbonyl]-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester

Procedure

N-[3-[(Benzyloxy)carbonyl]-N-[N-(t-butoxycarbonyl)-β-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester was deprotected and coupled with 5-cyano-2-pyridinecarboxylic acid to give N-[3-[(benzyloxy)carbonyl]-N-[N-[(5-cyano-2-pyridyl)carbonyl]-β-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester, m.p. 157°-158° C.

Sources & evidence

ORD record
ord-f19b58f18781411a99c980dbd22087d0
Source dataset
uspto-grants-1995_07
Patent number
US05430024

Reaction notes

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