Ethyl formate → (2S)-2-formylamino-propionic acid tert-butyl ester

HRID 602927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602927
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH:21](OCC)=[O:22]>C(Cl)Cl>[C:2]([O:6][C:7](=[O:11])[C@@H:8]([NH:9][CH:21]=[O:22])[CH3:10])([CH3:5])([CH3:4])[CH3:3]

Komponenten

5

Edukt 3

HCID 8025Ethyl formateHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochloride

Produkt 1

HCID 79006784(2S)-2-formylamino-propionic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of (2S) alanine tert-butyl ester hydrochloride (3.63 g, 20 mmol) in a mixture of ethyl formate (10 mL) and DCM (5 mL) was added diisopropylethylamine (3.83 mL, 22 mmol) and the reaction mixture was refluxed overnight. The solvents were evaporated and the residue was then triturated in Et2O and filtrated. The filtrates were evaporated and the residue was filtered through a short pad of silica using ethyl acetate as eluent. Evaporation of the solvent afforded the sub-title compound as a colorless oil which crystallised upon standing (2.806 g, 81%): 1H NMR (400 MHz CDCl3) δ 1.43 (3H, d), 1.50 (9H, s), 4.55 (1H, m), 6.31 (1H, br s), 8.16 (1H, s).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvents were evaporated
  3. customthe residue was then triturated in Et2O
  4. filtrationfiltrated
  5. customThe filtrates were evaporated
  6. filtrationthe residue was filtered through a short pad of silica
  7. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-1dd566a3561044b79407989becf4d1d7
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906650B2

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