Sodium Hydroxide → HCID 10137601, compound

HRID 2184341Notes

Reaction equation

HRID 2184341 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[C@@H:15](/[CH:16]=[CH:17]/[CH:18]([OH:28])[C:19]2[O:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=2)[CH2:14][C:13]([CH3:30])([CH3:29])[C:12]1=[O:31])C.[OH-].[Na+]>CO>[OH:28][CH:18]([C:19]1[O:20][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:23]=1)/[CH:17]=[CH:16]/[C@@H:15]1[N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:32])=[O:3])[C:12](=[O:31])[C:13]([CH3:30])([CH3:29])[CH2:14]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59075085HCID 59075085, compound

Product 1

HCID 10137601HCID 10137601, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-{(R)-5-[(E)-3-hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-3,3-dimethyl-2-oxo-pyrrolidin-1-yl}-heptanoic acid ethyl ester (89 mg, 0.2 mmol) was dissolved in methanol (3 mL) and the solution cooled in an ice bath. A 20% solution of sodium hydroxide (0.280 mL, 1.4 mmol) was slowly added and when the addition was complete, the reaction flask was left stirring overnight at room temperature. The reaction solution was concentrated under vacuum; the residue was suspended in 5 mL of 0.1 N solution of sodium hydroxide and it was washed twice with diethyl ether. The solution was then acidified with 1 N hydrochloric acid and extracted three times with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate giving after concentration 55 mg of 7-{(R)-5-[(E)-3-hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-3,3-dimethyl-2-oxo-pyrrolidin-1-yl}-heptanoic acid (55) (80). MS: 432 [(M+H)+].

Workup

  1. temperaturethe solution cooled in an ice bath
  2. additionwhen the addition
  3. waitthe reaction flask was left
  4. concentrationThe reaction solution was concentrated under vacuum
  5. washwas washed twice with diethyl ether
  6. extractionextracted three times with ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried over magnesium sulfate giving after concentration 55 mg of 7-{(R)-5-[(E)-3-hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-3,3-dimethyl-2-oxo-pyrrolidin-1-yl}-heptanoic acid (55) (80)

Sources & evidence

ORD record
ord-60a0bf6a177f4316ac61daceae2f86e2
Source dataset
uspto-grants-2005_05
Patent number
US06900336B2

Reaction notes

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