Sodium methanesulfinate → [(R)-4-(3-methanesulfonyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester

HRID 2387539ノート

反応式

HRID 2387539 の反応式
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21](Br)[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2].[Na+].[CH3:32][S:33]([O-:35])=[O:34].[Na+].N1CCC[C@H]1C([O-])=O>CS(C)=O.O.[Cu]I>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][S:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([S:33]([CH3:32])(=[O:35])=[O:34])[CH:20]=3)(=[O:18])=[O:17])[C:9]=2[CH:8]=[N:7]1)[CH3:2]

参加物

7

反応物 3

HCID 2733271Sodium methanesulfinateHCID 23678551L-Proline sodium saltHCID 44611775HCID 44611775、化合物

生成物 1

HCID 59152955[(R)-4-(3-methanesulfonyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester収率 51.1%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

反応条件

温度
150 °C

実験手順

[(R)-4-(3-Bromo-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]acetic acid ethyl ester (118.0 mg, 0.20 mmol), methanesulfinic acid sodium salt (24.5 mg, 0.24 mmol), copper(I) iodide (4.0 mg, 0.02 mmol) and L-proline sodium salt (3.2 mg, 0.04 mmol) were dissolved in dimethyl sulfoxide (1.5 mL) and water (0.3 mL). The mixture was heated in a microwave oven at 150° C. for 30 minutes. The resulting mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by column chromatography (gradient elution, 0-5% methanol in dichloromethane) to afford [(R)-4-(3-methanesulfonyl-5-trifluoromethyl-benzenesulfonylamino)-4,5,6,7-tetrahydro-indazol-1-yl]-acetic acid ethyl ester (52.0 mg, 51.1%) as a white solid. MS calcd. for C19H22F3N3O6S2 509, obsd. (ESI+) [(M+H)+] 510.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography (gradient elution, 0-5% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-a1dd041d9ee84a93a425f0afdf85cca8
出典データセット
uspto-grants-2012_09
特許番号
US08268870B2

反応ノート

読み込み中…