Isobutyl chloroformate → BocLeu-DMetNH2

HRID 2418543Notes

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][S: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][S:21][CH3:22])=[O:9])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

Reactant 3

HCID 62365Isobutyl chloroformate

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-

HCID 11571827HCID 11571827, compound

Product 1

HCID 92232527BocLeu-DMetNH2Yield 70%

Procedure

Condensation of BocLeuOH (3.49 g.) and HDMetNH2 (2.0 g.) by the mixed anhydride method using isobutyl chloroformate gave BocLeu-DMetNH2 in 70% yield. De-t-butoxycarbonylation of BocLeu-DMetNH2 (2.74 g.) using hydrogen chloride in ethyl acetate gave HLeu-DMetNH2 in 91% yield. Condensation of BocGlyOSu (2.66 g.) and HLeu-DMetNH2 (1.95 g.) by the active ester method gave BocGly-Leu-DMetNH2 in 92% yield. De-t-butoxycarbonylation of BocGly-Leu-DMetNH2 (2.30 g.) using hydrogen chloride in acetic acid gave HGly-Leu-DMetNH2 in 79% yield.

Sources & evidence

ORD record: ord-62db4a6b4c4849d5a14f035f819d11a3
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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