Trifluoroacetic acid → {1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

HRID 1965169노트

반응식

HRID 1965169 반응식
C(OC([N:8]1[CH2:12][CH:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=2)[CH:10]2[N:22]([C:25](=[O:42])[CH:26]([NH:31][C:32]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:23][CH2:24][CH:9]12)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)Cl.CO>C(Cl)Cl>[CH2:35]([O:34][C:32](=[O:33])[NH:31][CH:26]([C:25]([N:22]1[CH2:23][CH2:24][CH:9]2[NH:8][CH2:12][CH:11]([O:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[C:16]([F:21])[CH:15]=3)[CH:10]12)=[O:42])[C:27]([CH3:30])([CH3:29])[CH3:28])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 676074394-(2-Benzyloxycarbonylamino-3,3-dimethyl-butyryl)-3-(3,4-difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carboxylic acid tert-butyl ester

생성물 1

HCID 67608719{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester수율 102%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

The Boc-containing compound 23 (1.0 g, 1.70 mmol) was dissolved in DCM (4 mL) and cooled to 0° C. before TFA (2 mL) was added and the reaction stirred at 0° C. for 1 h. TLC analysis (10:1 DCM/MeOH) indicated the starting material had all been consumed and the product had formed. The reaction mixture was concentrated at low pressure on the rotary evaporator. The crude residue was dissolved in DCM and washed successively with saturated aqueous NaHCO3 (3×), and brine. The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to afford 845 mg of 24 as a white foam. Mass spectrum, m/z [488.3] (M+H)+.

후처리

  1. additionwas added
  2. customall been consumed
  3. customthe product had formed
  4. concentrationThe reaction mixture was concentrated at low pressure on the rotary evaporator
  5. dissolutionThe crude residue was dissolved in DCM
  6. washwashed successively with saturated aqueous NaHCO3 (3×), and brine
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-300d8db8ee8743a88aac97e6f3e92512
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415486B2

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