Réaction #42355

ord-92306b3288f94584930245ab3ab8e0d5

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

CO.c1ccccc1
methanol benzene

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe solution is concentrated under reduced pressure

Mode opératoire

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]+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07727997B2uspto-grants-2010_06