Hydrochloric Acid → HCID 76168100, compound

Reaction equation

[CH3:1][N:2]([CH3:27])[C:3]([CH2:5][O:6][N:7]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[C:8](=[O:18])[CH:9]=[C:10]1[C:14](=[O:15])[O:13]C(C)(C)[O:11]1)=[O:4].[OH-].[Li+].Cl>O1CCCC1>[CH3:27][N:2]([CH3:1])[C:3]([CH2:5][O:6][N:7]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[C:8]([CH:9]=[C:10]([OH:11])[C:14]([OH:15])=[O:13])=[O:18])=[O:4]

Participants

Procedure

A solution of N-dimethylcarbamoylmethoxy-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-(4-fluorobenzyl)-acetamide (0.065 g, 0.17 mmol in tetrahydrofuran (3 ml) was treated at 0° C. with 0.34 ml (0.34 mmol) of 1 M aqueous lithium hydroxide. After 1 h, the reaction mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried (magnesium sulphate) and evaporated in vacuo. Crystallisation of the residual solid from a mixture of ethyl acetate and hexane gave 0.043 g (74% yield) of the title material as a white solid: mp 118-120° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm); (mixture of enol and keto forms, 7:3); enol form: 2.83 (3H, s, NCH3), 2.88 (3H, s, NCH3), 4.79 (2H, s, CH2), 4.94 (2H, s, CH2), 6.47 (1H, s, CH), 7.18 (2H, m, aromatics), 7.38 (2H, m, aromatics), 13.2 (1H, broad, OH), 13.7 (1H, broad, OH). HRMS (ES+) calculated for C15H18FN2O6[M+H]+: 341.114890. Found: 341.115095.