Water → 4-(2-Isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl ester

HRID 1867990ノート

反応式

HRID 1867990 の反応式
CO[CH2:3][C:4]([NH:6][C:7]1[S:8][C:9]2[CH:15]=[C:14]([O:16][S:17]([C:20]3[CH:25]=[CH:24][C:23](F)=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5].[CH:27]([NH:30][CH2:31][CH2:32][NH2:33])([CH3:29])[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].O>CS(C)=O>[CH:3]1([C:4]([NH:6][C:7]2[S:8][C:9]3[CH:15]=[C:14]([O:16][S:17]([C:20]4[CH:21]=[CH:22][C:23]([NH:33][CH2:32][CH2:31][NH:30][CH:27]([CH3:29])[CH3:28])=[CH:24][CH:25]=4)(=[O:19])=[O:18])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:12][CH2:10][CH2:9][CH2:15]1

参加物

6

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 88098N-IsopropylethylenediamineHCID 579808544-Fluorobenzenesulfonic acid 2-(2-methoxy-acetylamino)benzothiazol-6-yl ester2 回

生成物 1

HCID 579808394-(2-Isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl ester収率 48.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A solution of 4-fluorobenzenesulfonic acid 2-(2-methoxyacetylamino)-benzothiazol-6-yl ester (intermediate 68) (90 mg, 0.214 mmol), N-isopropylethylenediamine (65.6 mg, 0.642 mmol) and cesium carbonate (69.7 mg, 0.214 mmol) in 2 ml of dimethyl sulfoxide in a test tube, equipped with a magnetic bar, is stirred overnight at 80° C. 100 ml of water are added and the reaction medium is extracted with ethyl acetate. The organic phase is then washed with water, dried over magnesium sulfate and evaporated. The residue, purified by LC/MS, gives 26.2 mg of 4-(2-isopropylaminoethylamino)benzenesulfonic acid 2-(cyclopentanecarbonyl-amino)benzothiazol-6-yl ester (white powder) in a yield of 24%.

後処理

  1. extractionthe reaction medium is extracted with ethyl acetate
  2. washThe organic phase is then washed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue, purified by LC/MS

出典と根拠

ORDレコード
ord-5b5b3b01394f45129a079e55ce8a809f
出典データセット
uspto-grants-2009_12
特許番号
US07632952B2

反応ノート

読み込み中…