Benzathine → (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1805213

反応式

HRID 1805213 の反応式
[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:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[O:31])=[CH:25][CH:24]=1.[F-].[K+].C(NCCNCC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([NH:32][C:30]([NH:29][C:26]3[CH:27]=[CH:28][C:23]([Cl:22])=[CH:24][CH:25]=3)=[O:31])=[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

7

反応物 4

HCID 8793BenzathineHCID 87964-ChlorophenylureaHCID 522689Potassium FluorideHCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 67151498(RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester収率 14%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

A stirred suspension of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (1.60 g), 4-chlorophenylurea (0.81 g), potassium fluoride (2.88 g, 40 wt % on alumina), N,N′-dibenzylethylenediamine (0.14 ml) and copper(I) iodide (0.11 g) in THF (16 ml) in a sealed tube was heated at 90° C. for 30 minutes under microwave irradiation. The mixture was then cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-{4-[3-(4-chloro-phenyl)-ureido]-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.24 g, 14%) as a light yellow solid. MS (ISP): 392.1 ([{37Cl}M+H—C4H8]+), 390.1 ([{35Cl}M+H—C4H8]+).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

出典と根拠

ORDレコード
ord-07b2e2e9e8924e7a82757d4df75d472a
出典データセット
uspto-grants-2013_01
特許番号
US08354441B2

関連ノート

読み込み中…