Hydrochloric Acid → 2-(4-((R)-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl)butoxy)acetic acid

HRID 22975Notes

Reaction equation

C[O:2][C:3](=[O:25])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[C@@H:18]([OH:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[Li+].Cl>CO.C1COCC1.O>[OH:24][C@@H:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])/[CH:17]=[CH:16]/[C@H:11]1[CH2:12][CH2:13][C:14](=[O:15])[N:10]1[CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]([OH:25])=[O:2]

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid methyl ester (0.14 g, 0.4 mmol) in a mixture of 2 mL of methanol and 2 mL THF at room temperature under a nitrogen atmosphere was added an aqueous solution of lithium hydroxide (0.066 g, 1.6 mmol) in 1 mL of water. The reaction was stirred at 45° C. overnight, cooled to room temperature and treated with aqueous hydrochloric acid (1 M) until acidic. The residue was diluted with water (10 mL) and extracted with ethyl acetate. The organic solution was dried (brine, Na2SO4), evaporated and purified by chromatography to yield 28 mg of {4-[(R)-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-pyrrolidin-1-yl]-butoxy}-acetic acid; ESMS: m/z (M+) 341.

Workup

temperaturecooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe organic solution was dried (brine, Na2SO4)
customevaporated
custompurified by chromatography

Sources & evidence

ORD record: ord-a65f9d3fb99649e6a60dcd51f31c6f06
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849657B2

Reaction notes

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