Water → HCID 131734843, compound

Participants

Reaction Conditions

Reaction Steps

No. 5327507 (Compound C; 1.09 g, 1.27 mmol) was dissolved in acetonitrile (10.9 mL), and then water (0.109 mL), triethylamine (1.06 mL, 7.61 mmol), and lithium bromide (2.91 g, 33.5 mmol) were added at room temperature. The reaction solution was stirred at 50° C. for 3.5 hours, then cooled to room temperature, quenched by the addition of 1 M hydrochloric acid (30 mL), and then extracted with ethyl acetate (100 mL). The organic layer was washed twice with water (100 mL) and then with a saturated aqueous solution of sodium chloride (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain 1.08 g (purity 71%, ESI (LC/MS positive mode) m/z 845 (M+H); Rt 3.32 min.) of Compound I, tert-butyl (E)-(2S,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-carboxy-ethylcarbamoyl]-11-(2-heptyl-[1,3]dioxolan-2-yl)-2-hydroxy-undec-4-enoate as a crude product.

Provenance & Evidence