Hydrochloric Acid → HCID 67129726, compound

Participants

Reaction Conditions

Reaction Steps

The product from step 1 was dissolved in THF (200 mL) and cooled to 0° C. in an ice bath. Hydrogen peroxide (22.6 mL, 35%, 258 mmol), followed by LiOH (4.12 g, 172 mmol in 40 mL water) were added, and the mixture was allowed to warm to rt and stirred overnight to afford the acid intermediate [HPLC/MS: 323.2 (M+1); Rt=2.97 min]. To this solution was added aqueous HCl (21.5 mL, 12M) and the reaction was aged at 60° C. overnight. The reaction was cooled to rt and the organic phase was separated. The aqueous phase was extracted with EtOAc (200 mL). The organic portions were combined and dried with MgSO4, filtered and concentrated. The resulting crude product was dissolved in EtOAc (300 mL) and N-cyclohexylcyclohexanamine (18.9 mL, 95 mmol) was added over 2 min. The resulting slurry was aged for 1 h and filtered. The wet cake was washed with EtOAc (50 mL×4) and air dried on a fritted funnel. The salt was then suspended in aq NaHSO4 (200 mL, 2N) at rt and aged overnight. The reaction was extracted with EtOAc (200 mL), washed with water and brine, dried (MgSO4), filtered and concentrated to afford the title compound. HPLC/MS: 237.1 (M+1); Rt=2.13 min.

Provenance & Evidence