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Lithium Hydroxide → (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid

HRID 19408
Notes
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Reaction equation

HRID 19408 reaction equation
C([O:3][C:4](=[O:25])[C@@H:5]([N:11]1[CH2:15][C:14]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[CH:13][C:12]1=[O:24])[CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])C.[OH-].[Li+]>O1CCCC1>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH2:15][N:11]([C@@H:5]([CH2:6][CH:7]([CH3:10])[CH2:8][CH3:9])[C:4]([OH:25])=[O:3])[C:12](=[O:24])[CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66894874(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester

Product 1

HCID 66894966(S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid ethyl ester (0.95 g, 2.60 mmol) in tetrahydrofuran (15 mL) was treated with an aqueous 0.5N lithium hydroxide solution (10.4 mL) and stirred at 5° C. for 2 h. The mixture was concentrated in vacuo and the residue was dissolved in water (40 mL) and extracted with diethyl ether. The ether layer was discarded, and the aqueous layer was acidified with 1N aqueous hydrochloric acid (8 mL) and extracted with ethyl acetate. The combined ethyl acetate layers were concentrated in vacuo which afforded (S)-2-[4-(2-chloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-hexanoic acid (839 mg, 96%) as a pale orange solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (40 mL)
  3. extractionextracted with diethyl ether
  4. extractionextracted with ethyl acetate
  5. concentrationThe combined ethyl acetate layers were concentrated in vacuo which

Sources & evidence

ORD record
ord-b8ff6db2dcd5462eb611bb67c011f788
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07741327B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes