Methanol → (S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoate

HRID 929934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929934
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([O:15][CH3:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

Produkt 1

HCID 10444846(S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoateAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (10.0 g, 42.1 mmol) in methanol (100 mL) and toluene (300 mL) was added dropwise at room temperature under argon trimethylsilyldiazomethane (23.2 mL, 46.4 mmol). After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the residue was extracted with a solution of EtOAc and brine. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in hexane from 0% to 30% in order to give the title compound (5.2 g, 48%) as a colorless oil. LC-MS: [M+H] 252.1; Rt 0.93 min; (LCMS method 1).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. extractionthe residue was extracted with a solution of EtOAc and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (120 g SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-e7fbe75c337a42d5b27d29a09f6dcf0f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296733B2

Notizen zur Reaktion

Wird geladen…