Diethylamine → (3S)-3-amino-4-oxobutyric acid tert-butyl ester semicarbazone

HRID 363874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 363874
[C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][C@H:8]([NH:11]C(OCC1C2CC3C(=CC=CC=3)C=2C=CC=1)=O)[CH:9]=[O:10])([CH3:4])([CH3:3])[CH3:2].C(NCC)C>CN(C=O)C>[C:1]([O:5][C:6](=[N:29][NH:30][C:31]([NH2:33])=[O:32])[CH2:7][C@H:8]([NH2:11])[CH:9]=[O:10])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 8021DiethylamineHCID 566185953(S)-(1-fluorenylmethyloxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone

Produkt 1

HCID 53985399(3S)-3-amino-4-oxobutyric acid tert-butyl ester semicarbazone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(3S)-3-(1-Fluorenylmethyloxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone (210 mg, 0.45 mol, Prepared in a similar manner to the benzyloxycarbonyl analog in Graybill et al., Int. J. Protein Res., 44, pp. 173-82 (1994).) was dissolved in 10 ml of DMF and 2 ml of diethylamine and stirred for 2 h. The reaction was concentrated in vacuo to give (3S)-3-amino-4-oxobutyric acid tert-butyl ester semicarbazone. The 0° C. solution of the above residue and 603a (200 mg, 0.42 mmol) in 5 ml of DMF and 5 ml of CH2Cl2 was treated with 1-hydroxybenzotriazole (57 mg, 0.42 mmol) and 1-(3-dimethylaminopropyl)-3ethylcarbodiimide hydrochloride (98 mg, 0.51 mmol). The reaction was stirred at RT for 18 h, poured onto EtOAc (75 ml) and washed with aq. 0.3N KHSO4, sat. aq. NaHCO3 and sat. aq. NaCl, dried over NaSO4 and concentrated in vacuo. Chromatography (flash, SiO2, 0% to 4% MeOH/0.1% NH4OH/CH2Cl2) to give 240 mg (83%) of 604a.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ee0c59d28bdf40d3bdbf382de27b8c9a
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05874424

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