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Lithium Hydroxide → 3-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid

HRID 430277
Notes
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Reaction equation

HRID 430277 reaction equation
C([O:3][C:4](=[O:23])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=1)[CH2:6][CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[Li+]>O1CCCC1>[CH:7]1([CH2:6][CH:5]([C:12]2[CH:17]=[CH:16][C:15]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[C:4]([OH:23])=[O:3])[CH2:11][CH2:10][CH2:9][CH2:8]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 543970993-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 223152063-Cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid ethyl ester (2.50 g, 7.39 mmol) in tetrahydrofuran (30 mL) was treated with a 0.8M aqueous lithium hydroxide solution (11.1 mL, 8.86 mmol). The reaction mixture was stirred at 25° C. for 23 h. The resulting reaction mixture was partitioned between water (75 mL) and ethyl acetate (75 mL) and then treated with a 1N aqueous hydrochloric acid solution (15 mL). The layers were shaken and separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-(4-ethanesulfonyl-phenyl)-propionic acid (2.20 g, 96%) as a white solid which was used without further purification: mp 137-138° C.; FAB-HRMS m/e calcd for C16H22O4S (M+H)+ 311.1317, found 311.1321.

Workup

  1. customThe resulting reaction mixture
  2. customwas partitioned between water (75 mL) and ethyl acetate (75 mL)
  3. additiontreated with a 1N aqueous hydrochloric acid solution (15 mL)
  4. stirringThe layers were shaken
  5. customseparated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91f748a2042a44898b3cfd6bb607e1a7
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06320050B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes