Lithium hydroxide, monohydrate → HCID 67191150, compound

HRID 546204Notes

Reaction equation

HRID 546204 reaction equation
C[O:2][C:3](=[O:24])[C@@H: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][C@@H:6]1[CH2:10][CH2:9][C:8]([F:12])([F:11])[CH2:7]1.O.[OH-].[Li+]>C(O)C.O>[Cl:23][C:15]1[CH:14]=[C:13]([CH:4]([CH2:5][C@@H:6]2[CH2:10][CH2:9][C:8]([F:12])([F:11])[CH2:7]2)[C:3]([OH:24])=[O:2])[CH:18]=[CH:17][C:16]=1[S:19]([CH3:22])(=[O:20])=[O:21]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67189629HCID 67189629, compound

Product 1

HCID 67191150HCID 67191150, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

(R)-2-(3-Chloro-4-methanesulfonyl-phenyl)-3-((S)-3,3-difluoro-cyclopentyl)-propionic acid methyl ester (224 mg, 0.59 mmol) was dissolved in ethanol (8 mL) and treated with a solution of lithium hydroxide monohydrate (62 mg, 1.47 mmol) in water (2 mL) at 25° C. It was stirred at 25° C. until the starting material was all consumed by TLC (˜1 hr). The reaction was then concentrated in vacuo to remove the ethanol. The remaining aqueous layer was then acidified to pH=2 with an aqueous 1N hydrochloric acid solution. This was then extracted with ethyl acetate (3×20 mL), the organic layers combined and dried over magnesium sulfate, filtered and concentrated in vacuo to afford 2-(3-chloro-4-methanesulfonyl-phenyl)-3-((S)-3,3-difluoro-cyclopentyl)-propionic acid (210 mg, 97%) as a mixture of two diastereomers as a clear colorless oil.

Workup

  1. customall consumed by TLC (˜1 hr)
  2. concentrationThe reaction was then concentrated in vacuo
  3. customto remove the ethanol
  4. extractionThis was then extracted with ethyl acetate (3×20 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de3be714484647f5aed6657b11b1b5c4
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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