Sodium Hydroxide → 1298053-61-8

Participants

Reaction Steps

Compound 31 (1 equivalent) was dissolved in dichloromethane, cooled to 5° C. and trifluoroacetic acid (2-3 w/v) was added and stirred at room temperature for 4h. The reaction mixture was concentrated and the residue dissolved in dimethylfomamide and cooled to 5° C. before addition of diisopropylethyl amine (10 equivalents). TBTU (1.8 equivalents) was added followed by 3,3-difluoropiperidine hydrochloride (1.2 equivalents). The reaction was stirred until completion and added to 1M citric acid and solid collected by filtration. The solid was crystallized from ethylacetate/heptane to give ACH-0142684 (purity >98%). ACH-0142684 was suspended in methanol and aqueous sodium hydroxide (1.05 equivalents) was added at about 5° C. to give a clear solution. The reaction mixture was concentrated to dryness and the residue was stirred with IPA to give crystalline ACH-0142684.Na (Form G). The crystalline ACH-0142684.Na was dissolved in a mixture of methanol/ethyl acetate and the solution was added to pentane. The solid was collected by filtration and dried to give ACH-0142684.Na in the amorphous form (purity >98%).

Provenance & Evidence