Methanol → HCID 22261409, compound

HRID 1610706Notes

Reaction equation

HRID 1610706 reaction equation
[F:1][CH:2]([C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][CH:28]=1)[CH2:10][CH:11]([CH:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[OH:18])[C:12]([O:14]CC)=[O:13])[C:3]([F:6])([CH3:5])[CH3:4].[OH-].[Na+].[CH3:31]O.O>O1CCCC1>[F:1][CH:2]([C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][CH:28]=1)[CH2:10][CH:11]([CH:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[OH:18])[C:12]([OH:14])=[O:13])[C:3]([F:6])([CH2:4][CH3:31])[CH3:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 86593301HCID 86593301, compound

Product 1

HCID 22261409HCID 22261409, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (2RS,3RS)-2-[3-(1,2-difluoro-2-methylpropyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionate (2.849 g, 7.223 mmol), sodium hydroxide (0.58 g, 14.4 mmol), methanol (10 ml), water (10 ml) and tetrahydrofuran (10 ml) was stirred overnight at room temperature. The reaction solution was concentrated, diluted with water, acidified with hydrochloric acid, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product of (2RS,3RS)-2-[3-(1,2-difluoro-2-ethylpropyl)benzyl]-3-(4-fluorophenyl)-3-hydroxypropionic acid as a liquid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7c922da68c864889a2e045a27812314a
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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