Sodium Hydroxide → 2-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxymethyl}-2-nitro-propane-1,3-diol

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-[4-(2,2-dimethyl-5-nitro-[1,3]dioxan-5-ylmethoxy)-3,5-dimethyl-phenyl]-5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazole (85 mg, 0.158 mmol) in THF:TFA:water 20:4:1 (12.5 mL) is stirred at 65° C. for 4.5 h. The mixture is further diluted with TFA:water 2:1 (1.5 mL) and stirring is continued at 65° C. for 3 h. The mixture is cooled to rt, poured onto 2N aq. NaOH and extracted twice with DCM. The organic extracts are dried over MgSO4 and evaporated to give 2-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxymethyl}-2-nitro-propane-1,3-diol (78 mg) as a beige resin; LC-MS: tR=1.17 min, [M+1]+=500.89.

Provenance & Evidence