Реакция #42355

ord-92306b3288f94584930245ab3ab8e0d5

Уравнение реакции

CC(C)(C)OC(=O)N[C@@H](CCOCc1ccccc1)C(=O)O
O-benzyl-N-(tert-butoxycarbonyl)homoserine
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazomethane
CCCCCC
hexane
→
COC(=O)[C@H](CCOCc1ccccc1)NC(=O)OC(C)(C)C
title compound
COC(=O)[C@H](CCOCc1ccccc1)NC(=O)OC(C)(C)C
Methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

Реактанты

CC(C)(C)OC(=O)N[C@@H](CCOCc1ccccc1)C(=O)O
O-benzyl-N-(tert-butoxycarbonyl)homoserine
C[Si](C)(C)C=[N+]=[N-]
trimethylsilyldiazomethane
CCCCCC
hexane

Реагенты

Нет

Растворители

CO.c1ccccc1
methanol benzene

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe solution is concentrated under reduced pressure

Методика

To O-benzyl-N-(tert-butoxycarbonyl)homoserine (5.8 g, 18.9 mmol) in 20% methanol/benzene (72 mL) is added 2M trimethylsilyldiazomethane in hexane (12.3 mL, 24.5 mmol), and the reaction stirred at room temperature 1.5 h. The solution is concentrated under reduced pressure to give the title compound in pure form. ESI MS m/z 324.2 [M+H]+.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07727997B2uspto-grants-2010_06