Sodium Hydroxide → HCID 86585364, compound

HRID 1954619Notes

Reaction equation

HRID 1954619 reaction equation
C([O:3][C:4]([C:6]1([C@H:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])[C:12](=[O:23])[C@H:11]2[F:24])[CH2:9][CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>CO>[C:4]([C:6]1([C@H:10]2[CH2:14][N:13]([C@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:12](=[O:23])[C@H:11]2[F:24])[CH2:7][CH2:8][CH2:9]1)([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86585362HCID 86585362, compound

Product 1

HCID 86585364HCID 86585364, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Cis 4-(1-ethoxycarbonylcyclobutyl)-3-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (optical isomer B; 1.79 g, 5.37 mmol) was dissolved in methanol (10 ml) to which was subsequently added dropwise a 1 N sodium hydroxide aqueous solution (10 ml). The reaction solution was stirred at 40° C. for 18 hours and then methanol was evaporated under reduced pressure. The thus obtained residue was mixed with water (50 ml) and washed with chloroform (100 ml). The thus separated aqueous layer was acidified by dropwise addition of 1 N hydrochloric acid and extracted with chloroform (100 ml×2). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain the title compound quantitatively as a crude product.

Workup

  1. custommethanol was evaporated under reduced pressure
  2. additionThe thus obtained residue was mixed with water (50 ml)
  3. washwashed with chloroform (100 ml)
  4. additionThe thus separated aqueous layer was acidified by dropwise addition of 1 N hydrochloric acid
  5. extractionextracted with chloroform (100 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e5be7365885648f384da5d80de9ffa94
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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