Hydrochloric Acid → (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid

HRID 859208Notes

Reaction equation

C[O:2][C:3]([C@H:5]1[CH2:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:4].Cl>O1CCOCC1>[F:25][C:21]1[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=1)[CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([N:7]2[C:8](=[O:10])[CH2:9][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 25.61 g (74.6 mmol) of (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in 650 ml of dioxane is treated with 175 ml of hydrochloric acid (37%). The mixture is heated at 50° C. for 18 h in a closed flask. For the working-up, the solution is evaporated under reduced pressure to yield the crude acid as a yellow solid. For purification, the crude acid is triturated at 0° C. in 50 ml of ethyl acetate. The solid is collected on a filter funnel and then dried under high vacuum to yield 20.3 g (82% of theory) of (S)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid as a yellowish solid; MS: m/e=330 (M+H)+.

Workup

customthe solution is evaporated under reduced pressure
customto yield the crude acid as a yellow solid
customFor purification
customthe crude acid is triturated at 0° C. in 50 ml of ethyl acetate
customThe solid is collected on a filter funnel
customdried under high vacuum

Sources & evidence

ORD record: ord-7e3d3bb967894ef9b09627015877f72f
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07151111B2

Reaction notes

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