Methyl iodide → 53363-89-6

HRID 2418540Notes

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:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[H-].[Na+].[CH3:19]I>>[C:10]([N:1]([CH3:19])[C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11]

Participants

Reactant 3

HCID 6328Methyl iodide

HCID 24758Sodium hydride

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

Product 1

HCID 701055553363-89-6Yield 73%

Procedure

Methylation of BocLeuOH (12.5 g.) using sodium hydride and methyl iodide gave BocMeLeuOH in 73% yield. Condensation of BocMeLeuOH (3.7 g.) and HMetNH2 hydrochloride salt (2.8 g.) by the mixed anhydride method using isobutyl chloroformate gave BocMeLeu-MetNH2 in 56% yield. De-t-butoxycarbonylation of BocMeLeu-MetNH2 (3.3 g.) using hydrogen chloride in ethyl acetate gave MeLeu-MetNH2 in 64% yield.

Sources & evidence

ORD record: ord-0524d95f27054a3d9c9a20c3974753d3
Source dataset: uspto-grants-1984_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04472305

Reaction notes

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