Sodium Hydroxide → 4-(S)-(1-Carboxycyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone

HRID 1954637Notes

Reaction equation

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

Participants

Conditions

Temperature: 40 °C

Procedure

4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (12.56 g, 39.33 mmol) was dissolved in ethanol (120 ml) and a 1 N aqueous solution of sodium hydroxide (120 ml) was added dropwise thereinto. After stirring at 40° C. for 6 hours, ethanol was evaporated under reduced pressure. The residue was washed with chloroform (100 ml×2). Under ice cooling, the separated aqueous layer was acidified by adding dropwise 1 N hydrochloric acid thereinto and then extracted successively with chloroform (300 ml×2) and diethyl ether (300 ml). The combined organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain 10.24 g (89.4%) of the title compound as colorless needles.

Workup

customethanol was evaporated under reduced pressure
washThe residue was washed with chloroform (100 ml×2)
additionby adding dropwise 1 N hydrochloric acid
extractionextracted successively with chloroform (300 ml×2) and diethyl ether (300 ml)
dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0148cf1131634a4091b9f2b4a544aed1
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121285

Reaction notes

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