Hydrochloric Acid → (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid
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][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:13][CH:12]=2)[CH2:6]1)=[O:4].Cl>O1CCOCC1>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][O:17][C:14]2[CH:13]=[CH:12][C:11]([N:7]3[C:8](=[O:10])[CH2:9][C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6]3)=[CH:16][CH:15]=2)=[CH:24][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 52 °C
Procedure
A solution of 1.27 g (3.7 mmol) of (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester in 77 ml of dioxane is treated with 8.64 ml of hydrochloric acid (37%). The mixture is heated at 52° 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 yellowish solid. For purification, the crude acid is triturated at −5° C. in 10 ml of ethyl acetate. The solid is collected on a filter funnel and then dried under high vacuum to yield 0.624 g (51% of theory) of (R)-1-[4-(4-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid as a white solid; MS: m/e=330 (M+H)+.
Workup
- customthe solution is evaporated under reduced pressure
- customto yield the crude acid as a yellowish solid
- customFor purification
- customthe crude acid is triturated at −5° C. in 10 ml of ethyl acetate
- customThe solid is collected on a filter funnel
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-4c4a70b058ae4ded8f20a9ec6f2d3b9b
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122562B2
Reaction notes
Loading…