tert-Butanol → 4-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

HRID 968675노트

반응식

HRID 968675 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH2:18]([O:25][C:26]1[C:27](C(O)=O)=[N:28][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([N:43]([CH2:46]C)CC)C.[CH3:48][C:49]([OH:52])([CH3:51])[CH3:50]>O1CCOCC1.CCOC(C)=O>[CH2:18]([O:25][C:26]1[C:27]([NH:43][C:46]([O:52][C:49]([CH3:51])([CH3:50])[CH3:48])=[O:8])=[N:28][N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69159267HCID 69159267, 화합물

생성물 1

HCID 691586054-Benzyloxy-3-(tert-butoxycarbonyl)amino-1-(2-fluorophenyl)pyrazole

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

실험 절차

Diphenylphosphoryl azide (2.16 mL) was added to a mixture of 4-benzyloxy-1-(2-fluorophenyl)pyrazole-3-carboxylic acid (2.09 g) and triethylamine (1.39 mL) in a mixture of 1,4-dioxane (25 mL) and tBuOH (25 mL). The mixture was refluxed for 1 hour and cooled to room temperature. The mixture was diluted with EtOAc and washed with H2O, 10% aq. citric acid, sat. NaHCO3 and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2) to yield 1.30 g of the title compound.

후처리

  1. temperatureThe mixture was refluxed for 1 hour
  2. washwashed with H2O, 10% aq. citric acid, sat. NaHCO3 and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexane 1/19, 1/9, 1/4 and 1/2)

출처 및 근거

ORD 기록
ord-6099d9d1ff0542e6ae4939ec054f48a1
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07304072B2

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