Reaktion #42355

ord-92306b3288f94584930245ab3ab8e0d5

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Lösungsmittel

CO.c1ccccc1
methanol benzene

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe solution is concentrated under reduced pressure

Vorschrift

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]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727997B2uspto-grants-2010_06