4-Toluenesulfonyl chloride → 2-Tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate

Participants

Reaction Steps

To a stirred suspension of 2-tert-butoxycarbonylamino-2-methyl-1-propanol (5.7 g, 30.11 mmol) and powdered NaOH (6.7 g, 0.151 mol) in Et2O (200 mL) was added p-toluenesulfonyl chloride (6.9 g, 36.14 mmol) at room temp. The stirred resulting mixture was heated under reflux for 8 hr. After cooling, ice-water (100 mL) was added to the solution. Separated Et2O layer was washed with brine, dried over Na2SO4, and evaporated. To the residue was added n-hexane and triturated. The solid was collected to afford 8.5 g (82.2%) 2-tert-butoxycarbonylamino-2-methyl-1-propyl p-toluenesulfonate as a crystalline material. 1H-NMR (CDCl3) δ1.26 (s, 6H), 1.38 (s, 9 H), 2.37 (s, 3H), 4.05 (s, 2H), 4.49 (br, 1H), 7.34 (d, J=7.8 Hz, 2H), 7.78 (d, J=7.8 Hz, 2H).

Provenance & Evidence