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Ethyl Acetate → (R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate

HRID 1771162
ノート
印刷プレビュー

反応式

HRID 1771162 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13].CC[N:21]([CH:25]([CH3:27])[CH3:26])C(C)C.[C:28]([O:31][CH2:32]C)(=[O:30])C>CN(C=O)C>[C:5]1([S:8][CH2:27][C@H:25]([NH:21][C:2]2[CH:7]=[CH:6][C:5]([S:8](=[O:10])(=[O:9])[NH2:11])=[CH:4][C:3]=2[S:12]([C:15]([F:18])([F:17])[F:16])(=[O:14])=[O:13])[CH2:26][C:28]([O:31][CH3:32])=[O:30])[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 250584524-Fluoro-3-((trifluoromethyl)sulfonyl)benzenesulfonamide2 回

生成物 1

HCID 66723774(R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate収率 56%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

4-Fluoro-3-(trifluoromethylsulfonyl)benzenesulfonamide (INTERMEDIATE 6, 21.67 g, 71.22 mmol) and DIPEA (129 ml, 738 mmol) were added to a solution of (R)-methyl 3-amino-4-(phenylthio)butanoate, trifluoroacetic acid salt (INTERMEDIATE 7, STEP 2) in DMF (20 ml). The resulting reaction mixture was heated at 50° C. for 1.5 hours, allowed to cool to room temperature, diluted with ethyl acetate (500 ml), and washed with water (250 ml) and brine (250 ml). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified by column chromatography (ISCO, eluting with 0→30% EtOAc/DCM over 54 minutes) to give the title product (20.5 g, yield: 56%).

後処理

  1. customThe resulting reaction mixture
  2. temperatureto cool to room temperature
  3. washwashed with water (250 ml) and brine (250 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe concentrate was purified by column chromatography (ISCO, eluting with 0→30% EtOAc/DCM over 54 minutes)

出典と根拠

ORDレコード
ord-243dbb3a4f1443dca3877ae081085f46
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09248140B2

反応ノート

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