Lithium Hydroxide → 4-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acid

HRID 1678623Notes

Reaction equation

HRID 1678623 reaction equation
C([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:37])[C:13]([C:21]2[N:22]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[N:23]=[C:24]3[C:29]=2[CH2:28][CH2:27][CH2:26][CH2:25]3)([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[OH:14])=[C:7]([F:38])[CH:6]=1)C.[OH-].[Li+]>C1COCC1.CO>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([N:22]2[C:21]([C:13]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)([OH:14])[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:39])=[O:3])=[CH:6][C:7]=3[F:38])=[O:37])=[C:29]3[C:24]([CH2:25][CH2:26][CH2:27][CH2:28]3)=[N:23]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 671309474-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acid ethyl ester

Product 1

HCID 451103854-{2-[2-(4-Chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acidYield 121%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-2-hydroxy-acetylamino}-3-fluoro-benzoic acid ethyl ester (6 mg, 11 μmol) in THF/MeOH 1/1 (0.2 ml) was a added a 1 N aqueous lithium hydroxide solution (60 μl, 60 μmol) at ambient temperature under an argon atmosphere. The reaction mixture was stirred for 12 h at ambient temperature and poured onto ice water/1 N aqueous NaOH solution 1/1. The layers were separated, the aqueous layer was acidified with ice cold 1 N aqueous HCl solution and extracted two times with iPrOAc. The combined extracts were washed with ice water/brine 1/1 and dried over Na2SO4. After filtration the solvent was removed under reduced pressure to give the title compound (7 mg; quant.) as yellow solid. MS: m/e=526.4 [M+H+].

Workup

  1. additionpoured onto ice water/1 N aqueous NaOH solution 1/1
  2. customThe layers were separated
  3. extractionextracted two times with iPrOAc
  4. washThe combined extracts were washed with ice water/brine 1/1
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure

Sources & evidence

ORD record
ord-933f7e74030d439bb1c401d0c947c200
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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