Isobutyl chloroformate → HCID 178446043, compound

HRID 1532794Notes

Reaction equation

HRID 1532794 reaction equation
N1C(=O)[C@H](CC2N=CNC=2)NC(=O)[C@@H]1CC(C)C.[CH2:19]([O:26][C:27]([NH:29][C@H:30]([C:35]([OH:37])=O)[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH2:38][C@H:39]([C:46]([OH:48])=[O:47])[CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1.ClC(OCC(C)C)=O>>[CH2:19]([O:26][C:27]([NH:29][C@H:30]([C:35]([NH:38][C@H:39]([C:46]([OH:48])=[O:47])[CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1)=[O:37])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 4

HCID 62365Isobutyl chloroformateHCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 178419078HCID 178419078, compoundHCID 178445852HCID 178445852, compound

Product 1

HCID 178446043HCID 178446043, compound

Procedure

The cyclic dipeptide, cyclo-(Leu-His) is a known substance [F. Schneider, Hoppe-Seyler's Z. Phys. Chem. 338, 131 (1964)], which can be prepared according to the usual peptide synthesis. For example, condensation between N-benzyloxycarbonyl-(S)-leucine and methyl ester of (S)-histidine in the presence of isobutyl chloroformate is effected in accordance with the mixed acid anhydride process to obtain methyl ester of N-benzyloxycarbonyl-(S)-leucyl-(S)-histidine and then the ester is hydrogenolyzed in the presence of palladium-carbon, followed by cyclization under reflux in methanol.

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-46e96a02732e44bc8ee495a9a401989b
Source dataset
uspto-grants-2001_03
Patent number
US06204406B1

Reaction notes

Loading…