Sodium Hydroxide → 3-[4-{2-(4-[Tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid methyl ester

Participants

Reaction Steps

Sodium hydroxide (0.045 g; 1.25 mmole) was pulverized and added to DMSO (10 ml). 2-Ethylsulfanyl-3-(4-hydroxyphenyl)propanoic acid methyl ester (0.21 g; 0.87 mmole) was added followed by addition of 2-[4-(tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.342; 0.87 mmole). The reaction mixture was stirred at room temperature for 3 hours then all the starting material were consumed according to LC-MS. Water (10 ml) and tetrahydrofuran (5 ml) were added and the stirring was continued over night. Then the reaction mixture was treated with diethyl ether and water and in order to avoid foam formation diluted hydrochloric acid was added. The phases were separated and the organic phase was washed three times with water. The water phases were combined and washed once again with diethyl ether. All the organic phases were combined, dried with sodium sulfate and evaporated. Chromatography in ether:petroleum ether (1:9 and 1:3) gave 0.18 g (41.4% yield) of 3-[4-{2-(4-[tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethylsulfanylpropanoic acid methyl ester.

Provenance & Evidence