4-Chlorobenzamide → (RS)-4-[4-(4-chloro-benzoylamino)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	4-Chlorobenzamide	HCID 12084	—
反応物	Potassium Phosphate, Tribasic	HCID 62657	—
反応物	(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester	HCID 67151644	—
触媒	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
溶媒	Dimethyl Sulfoxide	HCID 679	—
生成物	(RS)-4-[4-(4-chloro-benzoylamino)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester	HCID 67151477	69.5%

反応条件

温度	110 °C

反応手順

A stirred suspension of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (400 mg, Example 1e), 4-chlorobenzamide (185 mg), copper(I) iodide (20 mg), N,N′-dimethylglycine (20 mg) and potassium phosphate (1.05 g) in DMSO (2 ml) in a sealed tube was heated at 110° C. overnight. The mixture was then cooled to room temperature and was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-[4-(4-chloro-benzoylamino)-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (297 mg, 69%) as a white solid. MS (ISP): 450.2 ([{37Cl}M+NH4]+), 448.2 ([{35Cl}M+NH4]+), 433.2 ([{37Cl}M+H]+), 431.2 ([{35Cl}M+H]+), 377.2 ([{37Cl}M+H—C4H8]+), 375.2 ([{35Cl}M+H—C4H8]+).

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US08354441B2
出典データセット	uspto-grants-2013_01
ORD ID	ord-aa757563765243a58329c3ca90d0a859
出典メモ	uspto-grants-2013_01