N-(tert-Butyloxycarbonyl)-D-methionine → methyl Boc-D-methionyl-glycinate

HRID 3785Notes

Reaction equation

HRID 3785 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22]>>[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH:22][C:14](=[O:16])[C@@H:9]([CH2:10][CH2:11][S:12][CH3:13])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

Participants

3

Reactant 2

HCID 111051N-(tert-Butyloxycarbonyl)-D-methionineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 13216971methyl Boc-D-methionyl-glycinate

Procedure

The title compound was prepared by the general method of Example 1 using 24.9 g (0.1 mole) of t-butoxycarbonyl-D-methionine (BOC-D-Met) and 13.8 g (0.11 mole) of glycine methyl ester hydrochloride. The crude product was recrystallized from ethyl acetate/Skellysolve B to give the title compound, which was used in subsequent reactions without further purification.

Workup

  1. customThe crude product was recrystallized from ethyl acetate/Skellysolve B

Sources & evidence

ORD record
ord-df3ebfe50c8c461e85592be41123da00
Source dataset
uspto-grants-1988_02
Patent number
US04722922

Reaction notes

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