Pyridine → tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

HRID 1473714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473714
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1>ClCCl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]=[O:12])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 2

HCID 1049PyridineHCID 11054918(S)-tert-Butyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate

Produkt 1

HCID 10901762tert-Butyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-Butyl N-(tert-butoxycarbonyl)-L-homoserinate (1.00 g, 3.63 mmol) in dichloromethane (50 mL) was added at r.t. pyridine (0.88 mL, 10.9 mmol) and Dess-Martin-periodinane (2.31 g, 5.45 mmol). After 90 min the reaction mixture was diluted with ethyl acetate (40 mL), washed with 10% sodium thiosulphate solution (30 mL), saturated sodium bicarbonate solution (40 mL), and brine (40 mL). The combined aqueous layers were extracted with ethyl acetate (50 mL) and the combined organic layers were dried over sodium sulphate and concentrated under reduced pressure.

Aufarbeitung

  1. washwashed with 10% sodium thiosulphate solution (30 mL), saturated sodium bicarbonate solution (40 mL), and brine (40 mL)
  2. extractionThe combined aqueous layers were extracted with ethyl acetate (50 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-31d6d84e7af943bd8b0f60b0668c3388
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09017645B2

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