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

関与物質

役割	名称	HCID	仕込み量
反応物	Triethylamine	HCID 8471	—
反応物	1-Hydroxybenzotriazole	HCID 75771	—
反応物	Aminoacetaldehyde dimethyl acetal	HCID 89728	—
反応物	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
反応物	Z-Hyp(Tbu)-OH	HCID 6950951	—
溶媒	Water	HCID 962	—
溶媒	Dichloromethane	HCID 6344	—
生成物	(2S,4R)-4-tert-butoxy-2-(2,2-dimethoxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester	HCID 59548508	31.6%

反応手順

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.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US09403805B2
出典データセット	uspto-grants-2016_08
ORD ID	ord-071fe9db4ead4416b0834f1372cb66f2
出典メモ	uspto-grants-2016_08