Methyl morpholine oxide → HCID 58913253, compound

Participants

Reaction Steps

A mixture of 150 g (460 mmol) of ethyl 2-(2-tert-butoxycarbonylaminothiazol-yl)-4-pentenoate (Intermediate 34), 57 g (470 mmol) of N-methyl morpholine oxide and 1.0 g of osmium tetroxide in 1250 mL of 4/1 v/v acetone/water was stirred at RT for 1.5 h. To the mixture was added 100 g of solid sodium bisulfate and continued to stir for 0.5 h. The solid was removed by filtration and washing with acetone. The filtrates were combined and evaporated. The residue was diluted with 1000 mL of water and 2000 mL of ethyl acetate. The organic phase was separated and washed with brine (3×1000 mL), dried over Na2SO4 and condensed in vacuo. The residue was redissolved in 1500 mL of methanol and 1000 mL of water. 148 g of sodium periodate was added. The mixture was stirred for one hour, The solid was discarded by filtration and washing with methanol. The filtrates were condensed in vacuo and the reside was dissolved in 1000 mL of ethyl acetate. The organic layer was washed with brine (2×1000 mL), dried over Na2SO4 and evaporated until the solid formed. 1000 mL of hexane was added and the flask was allowed to stand at RT to let crystallization proceed. The solid was collected by filtration and washing with hexane and drying in vacuo. 79 g of the title compound was obtained as white solid. The mother liquid was condensed and the residue was suspended in hexane. A second crop of solid (24 g) was obtained as a yellow solid. The mother liquid was condensed again to afford a brown solid (22 g) which contained impurity.

Provenance & Evidence