Water → (+/-)-cis-({3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

At 40° C., add approx. 0.06 mmol of tetrabutylammonium hydrogensulphate and a solution of 200 mg (0.646 mmol) of (+/−)-cis-3-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol in 0.5 ml of toluene and 0.1 ml of THF to a mixture of 517 mg of 50% sodium hydroxide solution (6.5 mmol) and 0.5 ml of toluene. Admix the resulting mixture with 0.19 ml (1.29 mmol) of bromoacetic acid tert-butyl ester with vigorous stirring and heat it to 70° C. After 2 h, cool the mixture and add it to water. Extract three times with dichloromethane, wash the combined organic phases with saturated sodium chloride solution and concentrate under reduced pressure. After preparative RP-HPLC (eluent: acetonitrile/water), 152 mg (55.5% of theory) of the target product are isolated from the crude product.

Provenance & Evidence