Hydrochloric Acid → HCID 69921464, compound

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[CH2:11][C@@H:10]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C([O-])(O)=O.[Na+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][OH:14])[CH2:11][C@@H:10]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[CH:26][CH:27]=2)[C:9]1=[O:36])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Procedure

A solution of (3S,5R)-3-(4-benzyloxyphenyl)-5-(tert-butyldimethylsilanyloxymethyl)-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (2.0 g, 3.91 mmol) in tetrahydrofuran (45 mL) was cooled in an ice bath. Aqueous 0.5M HCl solution (7.8 mL, 3.9 mmol) was added and the resulting mixture was allowed to warm to room temperature while stirring overnight. After a total reaction time of 24 hours, saturated aqueous NaHCO3 solution was added. The mixture was extracted twice with diethyl ether and the combined organic phases were washed with brine, dried over MgSO4 and concentrated to an oil. The title compound, a colorless oil (1.02 g, 65%), was isolated by flash chromatography on silica gel eluting with 50% ethyl acetate in hexane.