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

HRID 363874노트

반응식

HRID 363874 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(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.

후처리

  1. concentrationThe reaction was concentrated in vacuo

출처 및 근거

ORD 기록
ord-ee0c59d28bdf40d3bdbf382de27b8c9a
출처 데이터셋
uspto-grants-1999_02
특허 번호
US05874424

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