Sodium Hydroxide → HCID 88111420, compound

HRID 1017762Notes

Reaction equation

HRID 1017762 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:13]([O:15][CH:16]2[CH2:20][CH2:19][CH:18]([C:21]([O:23]C)=[O:22])[CH:17]2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[OH-].[Na+]>CO>[F:1][C:2]([F:31])([F:32])[C:3]1[CH:4]=[C:5]([CH:13]([O:15][CH:16]2[CH2:20][CH2:19][CH:18]([C:21]([OH:23])=[O:22])[CH:17]2[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 87796836HCID 87796836, compound

Product 1

HCID 88111420HCID 88111420, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 905 mg of methyl 3-(SR)-(1-(RS)-(3,5-bis(trifluoromethyl)phenyl)-ethoxy)-2-(RS)-phenylcyclopentane-1-(RS)-carboxylate (lower Rf α-methyl isomer) (Racemic 2,3-trans isomer) from Example 8, Step D, Method A in 20 mL of methanol was added 5 mL of 2.0 N sodium hydroxide. After heating at reflux for 2 hours, the methanol was evaporated, and the residual liquid was acidified with 2 N hydrochloric acid. The aqueous phase was washed twice with ethyl acetate. The separate organic layers were washed with brine, combined, dried with sodium sulfate and evaporated to furnish 943 mg of the carboxylic acid.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 hours
  3. customthe methanol was evaporated
  4. washThe aqueous phase was washed twice with ethyl acetate
  5. washThe separate organic layers were washed with brine
  6. dry with materialdried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2c9b778a23a142deb1c36fa1ee2405ca
Source dataset
uspto-grants-2002_11
Patent number
US06479518B2

Reaction notes

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