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

HRID 1805217

反応式

[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH2:29])=[O:28])=[CH:25][CH:24]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CS(C)=O.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:29][C:27](=[O:28])[C:26]3[CH:30]=[CH:31][C:23]([Cl:22])=[CH:24][CH:25]=3)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

反応条件

温度: 110 °C

実験手順

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]+).

後処理

temperatureThe mixture was then cooled to room temperature
customwas purified by column chromatography (SiO2; gradient: heptane/EtOAc)

出典と根拠

ORDレコード: ord-aa757563765243a58329c3ca90d0a859
出典データセット: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08354441B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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