Sodium Hydroxide → HCID 45111943, compound

HRID 1678694Notes

Reaction equation

HRID 1678694 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH:12]([C:19]2[N:20]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[N:21]=[C:22]3[C:27]=2[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1.[OH-].[Na+]>CO.O>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([N:20]2[C:19]([CH:12]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:11][S:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:35])=[O:2])=[CH:9][CH:8]=3)=[C:27]3[C:22]([CH2:23][CH2:24][CH2:25][CH2:26]3)=[N:21]2)=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67130997HCID 67130997, compound

Product 1

HCID 45111943HCID 45111943, compoundYield 93.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a stirred solution of [rac]-4-{2-[2-(4-chloro-phenyl)-4,5,6,7-tetrahydro-2H-indazol-3-yl]-2-cyclohexyl-ethylsulfanyl}-benzoic acid methyl ester (22 mg, 0.043 mmol) in MeOH (5 ml) was added NaOH (5.18 mg, 0.129 mmol) in water (2 ml) dropwise at 0° C. The reaction mixture was then stirred at rt for 14 hours. After the completion of the reaction (monitored through TLC), MeOH was concentrated in vacuo, diluted with H2O (7 ml) and the aqueous layer was acidified (pH ˜2-3) with 2 N HCl and then extracted with EtOAc (3×7 ml). Combined organic layers were washed with brine (8 ml) and finally dried over Na2SO4. Organic layer was distilled under reduced pressure to get off white solid (20 mg), which was purified by column chromatography [SiO2 (230-400 mesh), DCM:MeOH 98.0/2.0] to give the title compound (18 mg, 84.1%) as a off white solid. MS: m/e=495.0 [M+H±].

Workup

  1. concentrationwas concentrated in vacuo
  2. additiondiluted with H2O (7 ml)
  3. extractionextracted with EtOAc (3×7 ml)
  4. washCombined organic layers were washed with brine (8 ml)
  5. dry with materialfinally dried over Na2SO4
  6. distillationOrganic layer was distilled under reduced pressure

Sources & evidence

ORD record
ord-c2c35c86da1d4c5eb4d39d22ff870dc7
Source dataset
uspto-grants-2011_08
Patent number
US08008505B2

Reaction notes

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