Reaktion #53965

ord-083d18281111497498375b85a4670b6f

Reaktionsgleichung

CC(C)[C@H](O)[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C
tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CC(C)[C@H](O)[C@H](NC(=O)OCc1ccccc1)C(=O)O
(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoic acid
Ausbeute 109.9%

Edukte

CC(C)[C@H](O)[C@H](NC(=O)OCc1ccccc1)C(=O)OC(C)(C)C
tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe volatiles were removed in vacuo

Vorschrift

A solution of tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate (400 mg, 1.19 mmol) in methylene chloride (7 ml) was cooled to 0° C. under nitrogen atmosphere. To this solution was added trifluoroacetic acid (10 ml), and the resulting mixture was warmed up to room temperature and stirred for 2.5 hours. The volatiles were removed in vacuo to provide (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoic acid (368 mg, 100%) as an orange oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858591B2uspto-grants-2005_02