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

HRID 243181ノート

反応式

HRID 243181 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-819546bebff748a3be6ee1f14c33d215
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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