Methanol → 1-(2'-t-Butoxycarbonyl-3-fluorobiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid
Reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[N:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:17][C:16]=2[F:34])[N:7]=1)=[O:5])C.CO.[Li+].[OH-]>>[C:30]([O:29][C:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:8]2[C:9]([CH2:11][CH2:12][CH3:13])=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]2)=[C:16]([F:34])[CH:17]=1)=[O:28])([CH3:31])([CH3:32])[CH3:33]Participants
4
Procedure
1-(2′-t-Butoxycarbonyl-3-fluorobiphenyl-4-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (758 mg, 1.6 mmol) was diluted with MeOH (10 mL, 0.2 mol), and LiOH (233 mg, 4.9 mmol) was added. The mixture was stirred overnight then concentrated to dryness. The residue was dissolved in DCM and water and the aqueous layer was neutralized with AcOH. The water layer was extracted with DCM and the combined organic layers were washed with saturated aqueous NaCl and dried over Na2SO4. The crude product was purified by flash chromatography (EtOAc in hexanes) to yield the title compound (710 mg).
Workup
- additionwas added
- concentrationthen concentrated to dryness
- dissolutionThe residue was dissolved in DCM
- extractionThe water layer was extracted with DCM
- washthe combined organic layers were washed with saturated aqueous NaCl
- dry with materialdried over Na2SO4
- customThe crude product was purified by flash chromatography (EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-e0a24c1d11f146f09ec9183a5023d48c
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822522B2
Reaction notes
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