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

HRID 327527Notes

Reaction equation

HRID 327527 reaction equation
[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH:29](C(OCC1C=CC=CC=1)=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[NH:11][C:12](=[O:28])[C@H:13]([CH3:27])[NH:14][C:15](=[O:26])[CH2:16][CH2:17][NH:18]C(OC(C)(C)C)=O)[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:55]([OH:57])=O)=[N:53][CH:54]=1)#[N:48]>>[CH2:1]([O:8][C:9](=[O:46])[C@H:10]([CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[NH:11][C:12](=[O:28])[C@H:13]([CH2:27][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:46])[NH:14][C:15](=[O:26])[CH2:16][CH2:17][NH:18][C:55]([C:52]1[CH:51]=[CH:50][C:49]([C:47]#[N:48])=[CH:54][N:53]=1)=[O:57])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 124007345-Cyanopyridine-2-carboxylic acidHCID 867474313-[(Benzyloxy)carbonyl]-N-[N-[N-(t-butoxycarbonyl)-beta-alanyl]-L-alanyl]-3-phenyl-L-alanine benzyl ester

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-[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-a187abe51e284f87ad3785fd424cd50a
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Reaction notes

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