Diisopropylethylamine → ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoate

HRID 749289Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749289
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@@H:7]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][OH:9])[CH3:2].C(N(C(C)C)CC)(C)C>CS(C)=O.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C@H:7]([CH:8]=[O:9])[NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH3:2]

Komponenten

4

Edukt 2

HCID 81531DiisopropylethylamineHCID 57351319Ethyl (4R)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentanoate

Produkt 1

HCID 57894011ethyl (4R)-4-(tert-butoxycarbonylamino)-4-formylbutanoateAusbeute 102,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23053668Dimethylsulfoxide ethyl acetateLösungsmittel

Versuchsvorschrift

Under an atmosphere of argon, to a mixed solution of (4R)-4-t-butoxycarbonylamino-5-hydroxypentanoic acid ethyl ester (1.62 g) and diisopropylethylamine (6.5 ml) in dimethylsulfoxide-ethyl acetate (1:1, 40 mL) was added sulfur trioxide pyridine complex (2.96 g) in ice bath and the mixture was stirred in ice bath for 1 hour. The reaction solution was poured into ice water and extracted with ethyl acetate. The organic layer was washed with 0.5N hydrochloric acid, water and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (1.65 g) having the following physical data.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 0.5N hydrochloric acid, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4f4647fb719047d1a39c66a37c2048f2
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402605B2

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