Triethyloxonium tetrafluoroborate → (S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate

HRID 243181노트

반응식

HRID 243181 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([C:11](=O)[NH2:12])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.C([O+](CC)CC)C.[F:27][C:28]1[CH:29]=[C:30]([NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:31](N)=[CH:32][CH:33]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([C:11]1[N:35]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:30]2[CH:29]=[C:28]([F:27])[CH:33]=[CH:32][C:31]=2[N:12]=1)[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 214506204-Fluoro-2-phenylaminoanilineHCID 45092008tert-Butyl (S)-(1-amino-1-oxobutan-2-yl)carbamate

생성물 1

HCID 68158046(S)-tert-butyl 1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propylcarbamate수율 54.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of ((S)-1-carbamoylpropyl)carbamic acid tert-butyl ester (300 mg, 1.48 mmol) in DCM (5 mL) was added triethyloxonium tetrafluoroborate (273 mg, 1.43 mmol) and the reaction mixture stirred at RT for 1.5 h under argon. The reaction mixture was concentrated in vacuo and the resulting residue dissolved in ethanol (3 mL). 4-Fluoro-N2-phenylbenzene-1,2-diamine (97 mg, 0.48 mmol) was added and the reaction heated at 70° C. for 1 h. The reaction mixture was concentrated in vacuo, and the resulting residue partitioned between DCM and sat. NaHCO3. The organic fraction was washed with brine, dried (Na2SO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (Si—PPC, gradient 0-20% EtOAc in cyclohexane) to afford the title compound as a pink foam (96 mg, 54%). LCMS (Method J): RT=3.70 min, [M+H]+=370.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resulting residue dissolved in ethanol (3 mL)
  3. temperaturethe reaction heated at 70° C. for 1 h
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. customthe resulting residue partitioned between DCM and sat. NaHCO3
  6. washThe organic fraction was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-819546bebff748a3be6ee1f14c33d215
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

반응 노트

불러오는 중…