N-(1,1-Dimethylethyl)benzenesulfonamide → N-(tert-Butyl)-2-(1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-3-hydroxypyrrolidin-3-yl)benzenesulfonamide

HRID 504370ノート

反応式

HRID 504370 の反応式
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:30]([N:32]3[CH2:36][CH2:35][C:34](=[O:37])[CH2:33]3)=[O:31])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1>CCCCC.CCOCC>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:34]1([OH:37])[CH2:35][CH2:36][N:32]([C:30]([C:27]2([C:24]3[CH:23]=[CH:22][C:21]([Cl:20])=[CH:26][CH:25]=3)[CH2:29][CH2:28]2)=[O:31])[CH2:33]1)(=[O:8])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 314059N-(1,1-Dimethylethyl)benzenesulfonamideHCID 666616461-{[1-(4-Chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-oneHCID 178418306HCID 178418306、化合物

生成物 1

HCID 11627061N-(tert-Butyl)-2-(1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}-3-hydroxypyrrolidin-3-yl)benzenesulfonamide

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8003Pentane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of N-(tert-butyl)benzenesulfonamide (569 mg, 0.00267 mol) in ether (10 mL, 0.1 mol) was added 1.7 M of tert-butyllithium in pentane (4.7 mL) under nitrogen at −78° C. The mixture was stirred at −78° C. for 15 minutes, then at 0° C. for 1 hour. The reaction mixture then was cooled down to −78° C. again and a solution of 1-{[1-(4-chlorophenyl)cyclopropyl]carbonyl}pyrrolidin-3-one (640 mg, 0.0024 mol) in ether was added. After stirring for 2 hours, the reaction mixture was quenched with saturated NH4Cl aqueous solution and then extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified using Combiflash eluting with 30% AcOEt in hexanes to afford the desired product. LC/MS (M+H+) 478.0.

後処理

  1. waitat 0° C. for 1 hour
  2. temperatureThe reaction mixture then was cooled down to −78° C. again
  3. stirringAfter stirring for 2 hours
  4. customthe reaction mixture was quenched with saturated NH4Cl aqueous solution
  5. extractionextracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude product was purified
  10. washeluting with 30% AcOEt in hexanes

出典と根拠

ORDレコード
ord-a46db8989a2949e29dc772d923f6b7c9
出典データセット
uspto-grants-2010_08
特許番号
US07776874B2

反応ノート

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