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

HRID 2275621노트

반응식

HRID 2275621 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8003Pentane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f35668f8fef141e7819ac16e85ba9179
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126927B2

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