Tert-Butylamine → ({3-[(1S)-2-tert-Butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoyl}oxy)(tert-butyl)ammonium

Participants

Reaction Steps

A solution of tert-butylamine was prepared by charging tert-butylamine (0.31 L, 2.94 mol) to a reaction vessel containing MTBE (2.27 L). The solution was stirred at ambient temperature and then charged into a second reaction vessel containing 3-[(1S)-2-tert-butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid (1.13 Kg, 267 mol) and MTBE (2.54 L). The temperature was maintained between 20-30° C. during the addition, the residual tert-butylamine was washed in with MTBE (0.57 L). The reaction mixture was heated to 38-40° C. for 3 hours under a nitrogen atmosphere. The reaction mixture was cooled to 18-25° C. over 1-2 hours and then held until crystallisation occurred. The product was isolated by filtration washed twice with MTBE (2.28 L), and dried in a vacuum oven at 38-40° C. This resulted in (1.32 Kg, 100% yield) of the title compound.

Provenance & Evidence