Methanol → HCID 22261777, compound

HRID 1610712Notes

Reaction equation

HRID 1610712 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([OH:29])[C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].CO.O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([OH:29])[C:23]([F:28])([F:27])[CH:24]([F:25])[F:26])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 86593304HCID 86593304, compound

Product 1

HCID 22261777HCID 22261777, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(2,2,3,3-tetrafluoro-1-hydroxypropyl)benzyl]propionate (5.878 g, 13.59 mmol), sodium hydroxide (1.09 g, 27.2 mmol), methanol (20 ml), water (30 ml) and tetrahydrofuran (20 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)-3-(4-fluorophenyl)-3-hydroxy-2-[3-(2,2,3,3-tetrafluoro-1-hydroxypropyl)benzyl]propionic 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-e47ef3ea5d604fe0a2063b02e760c51c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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