Methanesulfonyl chloride → HCID 86622510, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (1.55 g, 3.89 mmol) in DCM (60 mL) and DIPEA (1.07 mL, 6.22 mmol) is added methane sulfonylchloride (0.362 mL, 4.67 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min. Another portion of methane sulfonylchloride (0.362 mL, 4.67 mmol) is added and stirring is continued for 30 min. The reaction mixture is diluted with DCM, washed with 0.1 N aq. NaOH followed by 10% aq. citric acid solution, dried over MgSO4 and evaporated to give methanesulfonic acid 2-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenoxy}-ethyl ester (1.57 g) as an orange resin; LC-MS: tR=1.14 min, [M+1]+=477.35; 1H NMR (CDCl3): δ 6.86 (s, 2H), 4.57-4.50 (m, 2H), 4.05-4.00 (m, 2H), 3.10 8s, 3H), 3.03-2.85 (m, 5H), 2.79 (d, J=18.8 Hz, 1H), 2.37 8s, 3H), 2.25 (s, 6H), 1.92-1.85 (m, 2H), 1.11 (s, 3H), 0.70 (s, 3H).

Provenance & Evidence