Trifluoroacetic acid → (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoic acid

HRID 25687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 25687
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@@H:20]([OH:24])[CH:21]([CH3:23])[CH3:22])[C:13]([O:15]C(C)(C)C)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C@@H:20]([OH:24])[CH:21]([CH3:22])[CH3:23])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 59065895tert-butyl (2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoate

Produkt 1

HCID 69751905(2S,3S)-2-{[(benzyloxy)carbonyl]amino}-3-hydroxy-4-methylpentanoic acidAusbeute 109,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. customThe volatiles were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-083d18281111497498375b85a4670b6f
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858591B2

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