Cesium carbonate → 4-Chloro-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzenesulfonyl-(t-butoxycarbonyl)amino}-benzoic acid methyl ester

HRID 643991ノート

反応式

HRID 643991 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[N:11]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)(=[O:21])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH3:30][C:31]1[O:35][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][C:32]=1[CH2:42][CH2:43]OS(C)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[N:11]([S:19]([C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:43][CH2:42][C:32]2[N:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:35][C:31]=2[CH3:30])=[CH:26][CH:27]=1)(=[O:21])=[O:20])[C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 105407732-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonateHCID 685792122-[(4-Hydroxybenzene-sulfonyl)-(t-butoxycarbonyl)amino]4-chloro-benzoic acid methyl ester

生成物 1

HCID 685793864-Chloro-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzenesulfonyl-(t-butoxycarbonyl)amino}-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of the title E compound, 2-[(4-hydroxybenzenesulfonyl)-(t-butoxycarbonyl)-amino]-4-chloro-benzoic acid methyl ester (300 mg, 0.73 mmol), the title F compound, methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester (246 mg, 0.87 mmol) and cesium carbonate (475 mg, 1.46 mmol) is stirred in DMF at 60° C. overnight. The mixture is cooled and the product is taken up in EtOAc. The solution is washed with brine, dried over anhydrous magnesium sulfate, and concentrated to give the crude product which is purified by flash chromatography on silica gel using an EtOAc (15%)-hexane (85%) mixture as the eluent to afford 4-chloro-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzenesulfonyl-(t-butoxycarbonyl)amino}benzoic acid methyl ester as a white foam.

後処理

  1. temperatureThe mixture is cooled
  2. washThe solution is washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give the crude product which
  6. customis purified by flash chromatography on silica gel using an EtOAc (15%)-hexane (85%) mixture as the eluent

出典と根拠

ORDレコード
ord-109a54823d1d454090ca9b2c007d3fa9
出典データセット
uspto-grants-2010_04
特許番号
US07700637B2

反応ノート

読み込み中…