4-Cyanophenylacetic acid → HCID 53636466, compound

HRID 327505Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1)#[N:2].[NH2:13][CH2:14][CH2:15][C:16]([NH:18][C@H:19]([C:28]([NH:30][C@H:31]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:29])[CH2:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:17]>>[C:42]([O:41][C:39](=[O:40])[C@H:31]([CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[NH:30][C:28](=[O:29])[C@H:19]([CH2:20][C:21]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:27])[NH:18][C:16](=[O:17])[CH2:15][CH2:14][NH:13][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1)([CH3:43])([CH3:44])[CH3:45]

Participants

Reactant 2

HCID 795874-Cyanophenylacetic acid

HCID 131718293HCID 131718293, compound

Product 1

HCID 53636466HCID 53636466, compoundYield 51.5%

Procedure

142 mg of 4-cyanophenylacetic acid were coupled with 371 mg of H-β-Ala-Asp(O-tBu)-Phe-O-tBu (Example 1b) in the manner described in Example 1a), yielding 250 mg of N-[N-[N-(p-cyanophenylacetyl)-β-alanyl]-3-t-butoxycarbonyl-L-alanyl]-3-phenyl-L-alanine t-butyl ester, m.p. 93°-94° C., after chromatography on silica gel using ethyl acetate/methanol.

Sources & evidence

ORD record: ord-cc7ac41d38544a649f8d714cf2fef96f
Source dataset: uspto-grants-1993_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05273982

Reaction notes

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