Triethylamine → (2S,4R)-4-tert-butoxy-2-(2,2-dimethoxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

참여 물질

역할	이름	HCID	투입량
반응물	Triethylamine	HCID 8471	—
반응물	1-Hydroxybenzotriazole	HCID 75771	—
반응물	Aminoacetaldehyde dimethyl acetal	HCID 89728	—
반응물	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
반응물	Z-Hyp(Tbu)-OH	HCID 6950951	—
용매	Water	HCID 962	—
용매	Dichloromethane	HCID 6344	—
생성물	(2S,4R)-4-tert-butoxy-2-(2,2-dimethoxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester	HCID 59548508	31.6%

반응 단계

To a stirred solution of (2S,4R)-4-tert-butoxy-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (500 mg, 1.56 mmol) and 2,2-dimethoxy-ethylamine (163 mg, 1.56 mmol) in dichloromethane (5 mL) were added EDC-HCl (298 mg, 1.56 mmol), HOBt (210 mg, 1.56 mmol) and triethylamine (157 mg, 1.56 mmol). The mixture was stirred at room temp. for 24 h, diluted with water, extracted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography (using 15% EtOAc in hexane as eluent) to give (2S,4R)-4-tert-butoxy-2-(2,2-dimethoxy-ethylcarbamoyl)-pyrrolidine-1 -carboxylic acid benzyl ester (200 mg, 31.6% yield) as a light brown liquid. MS calcd. for C21H33N2O6 [(M+H)+] 409.0, obsd. 409.0.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09403805B2
출처 데이터셋	uspto-grants-2016_08
ORD ID	ord-071fe9db4ead4416b0834f1372cb66f2
출처 메모	uspto-grants-2016_08