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

HRID 968675Notes

Reaction equation

HRID 968675 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6099d9d1ff0542e6ae4939ec054f48a1
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

Loading…