Sodium Hydroxide → HCID 69509116, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(dimethylaminocarbonyl)oxyphenyl)propanoic acid ethyl ester (1.0 eq) in 3:1 MeOH/H2O was added 1M NaOH (2.5 eq). The mixture was stirred at 22° C. for 6 hr, and then the MeOH and H2O were evaporated. The residue was partitioned between Et2O and H2O, and then the separated aqueous layer was acidified to pH=3 by addition of 0.1 M H3PO4. The aqueous layer was extracted three times with 3:1 CHCl3/iPrOH, and then the CHCl3/iPrOH extracts were treated with MgSO4, filtered and evaporated to give (R)-3-(5-(2-fluorophenyl)-2-(N-cyclohexyl-N-methylamino)pyrimidin-4-ylamino)-3-(4-(dimethylaminocarbonyl)oxyphenyl)propanoic acid.

Provenance & Evidence