Lithium Hydroxide → 2-(3-Chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid

HRID 854837Notes

Reaction equation

HRID 854837 reaction equation
C[O:2][C:3](=[O:24])[CH:4]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:15]([Cl:23])[CH:14]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1.[OH-].[Li+]>CO.O>[Cl:23][C:15]1[CH:14]=[C:13]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]2)[C:3]([OH:24])=[O:2])[CH:18]=[CH:17][C:16]=1[S:19]([CH3:22])(=[O:21])=[O:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 674821092-(3-Chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid methyl ester

Product 1

HCID 219589672-(3-Chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acidYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid methyl ester (590 mg, 1.58 mmol) in methanol (7.0 mL) and water (3.0 mL) was treated with lithium hydroxide (980 mg, 31.6 mmol). The reaction mixture was stirred at 25° C. for 2 h and then concentrated in vacuo to remove methanol. The remaining aqueous layer was diluted with water (25 mL) and washed with ethyl acetate (2×50 mL). The aqueous layer was then acidified to pH=3 with a 1N aqueous hydrochloric acid solution and was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to afford pure 2-(3-chloro-4-methylsulfonyl-phenyl)-3-(4-oxo-cyclohexyl)-propionic acid (550 mg, 97%) as a colorless gum: EI-HRMS m/e calcd for C16H19ClO5S (M+Na)+ 381.0534. found 381.0537.

Workup

  1. concentrationconcentrated in vacuo
  2. customto remove methanol
  3. additionThe remaining aqueous layer was diluted with water (25 mL)
  4. washwashed with ethyl acetate (2×50 mL)
  5. extractionwas extracted with ethyl acetate (2×50 mL)
  6. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8925b104ac424c59a31e542a501035cd
Source dataset
uspto-grants-2007_08
Patent number
US07259166B2

Reaction notes

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