Isobutyl chloroformate → HCID 131713722, compound

HRID 2418553Notes

Reaction equation

HRID 2418553 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:17][C@H:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20][CH2:21][CH3:22].ClC(OCC(C)C)=O>>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:17][C@H:18]([C:23]([NH2:25])=[O:24])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 3

HCID 62365Isobutyl chloroformateHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 445699(2S)-2-aminohexanamide

Product 1

HCID 131713722HCID 131713722, compoundYield 75%

Procedure

Condensation of BocLeuOH (2.0 g.) and HNleNH2 (1.0 g.) by the mixed anhydride method using isobutyl chloroformate gave BocLeu-NleNH2 in 75% yield. De-t-butoxycarbonylation of BocLeu-NleNH2 (1.42 g.) using hydrogen chloride in dioxane gave HLeu-NleNH2 in 88% yield. Condensation of ZGlyOSu (1.91 g.) and HLeu-NleNH2 (0.95 g.) by the activated ester method gave ZGly-Leu-NleNH2 in 79% yield. Debenzyloxycarbonylation of ZGly-Leu-NleNH2 (1.40 g.) by hydrogenation with palladium catalyst gave HGly-Leu-NleNH2 in 67% yield.

Sources & evidence

ORD record
ord-02f43a6cf42c48dfa0b7f6323f794525
Source dataset
uspto-grants-1984_09
Patent number
US04472305

Reaction notes

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