Pyridine → (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid

Participants

Reaction Steps

12 μl of acetyl chloride and 22 μl of pyridine are added to 40 mg of tert-butyl (S)-3-methyl-2-{[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}butyrate in 0.5 ml of dichloromethane, and the mixture is stirred at room temperature for 18 h. The solution is then diluted with water and dichloromethane, the aqueous phase is removed and extracted with dichloromethane and the combined phases are dried over MgSO4 and concentrated. The residue is taken up in 0.5 ml of trifluoroacetic acid and allowed to stand at room temperature overnight. The solvent is distilled off completely and the residue is purified by HPLC, which gives 17 mg of (S)-2-{acetyl-[cis-3-(5-methyl-2-p-tolyloxazol-4-ylmethoxy)cyclohexylmethyl]amino}-3-methylbutyric acid. C26H36N2O5 (456.59); LCMS (ESI): 457.36 (MH+).

Provenance & Evidence