trans-2-Phenylcyclopropanecarboxylic acid → HCID 86752913, compound

HRID 1956978Notes

Reaction equation

HRID 1956978 reaction equation
Cl.C[O:3][C:4](=[O:29])[C@H:5]([CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)[NH:6][C:7](=[O:18])[C@@H:8]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH:9][CH3:10].[C:30]1([C@@H:36]2[CH2:38][C@H:37]2[C:39]([OH:41])=O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[C:30]1([C@@H:36]2[CH2:38][C@H:37]2[C:39]([N:9]([CH3:10])[C@@H:8]([C:7]([NH:6][C@H:5]([C:4]([OH:29])=[O:3])[CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)=[O:18])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:41])[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

3

Reactant 2

HCID 237413trans-2-Phenylcyclopropanecarboxylic acidHCID 67674832HCID 67674832, compound

Product 1

HCID 86752913HCID 86752913, compound

Procedure

Coupling of N-methyl-(D)-phenylalanyl-(L)-tryptophan methyl ester hydrochloride (see example 1) with trans-2-phenyl-1-cyclopropanecarboxylic acid according to example 12 followed by hydrolysis of the methyl ester moiety according to example 1 gives N-(trans-2-phenyl-1-cyclopropylcarbonyl)-N-methyl-(D)-phenylalanyl-(L)-tryptophan; FAB-MS m/e 510 (M+H)+.

Sources & evidence

ORD record
ord-339f0133667f4fddbe0d876eaac0b584
Source dataset
uspto-grants-1998_07
Patent number
US05780498

Reaction notes

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