Diethylamine → 3-Amino-4-oxobutyric acid tert-butyl ester semicarbazone

(3S) 3-(1-Fluorenylmethoxycarbonylamino)-4-oxobutyric acid tert-butyl ester semicarbazone (4; 226 mg, 0.5 mmol; prepared in a similar manner as the benzyloxycarbonyl analog described in Graybill et al. Int. J. Protein Res., 44, pp. 173-82 (1994)) was dissolved in 10 ml of acetonitrile (20 ml) and diethylamine (2 ml) was added to the solution. The reaction was stirred for two hours, concentrated in vacuo, the resulting dissolved in acetonitrile and concentrated in vacuo again to give (3S) 3-amino-4-oxobutyric acid tert-butyl ester semicarbazone. A 5° C. solution of the semicarbazone and 3 (188 mg, 0.424 mmol) in methylene chloride/DMF (6 ml of 1:1) was treated with 1-hydroxybenzotriazole (HOBt; 57 mg, 0.424 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDC; 115 mg, 0.6 mmol) and the reaction was stirred at room temperature for 16 hr. The reaction was diluted with ethyl acetate (100 ml) and washed with water, aqueous saturated NaHCO3 and aqueous saturated NaCl, dried over dried over anhydrous Na2SO4 and concentrated in vacuo. Chromatography (SiO2, 5% ammonium hydroxide/5% methanol/methylene chloride eluent) gave 250 mg of 5.

1. concentrationconcentrated in vacuo
2. dissolutionthe resulting dissolved in acetonitrile
3. concentrationconcentrated in vacuo again

ORDレコード

ord-29de97de76884803b23b7e6d7a4e1140

出典データセット

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06573259B2