Potassium Carbonate → HCID 57095368, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-[[4-[(3-methylphenyl)thio]phenyl]sulfonyl]-D-valine, 1,1-dimethylethyl ester, from Example 1c (3.96 g, 9.08 mmol) in 30 mL DMF was added 4-(2-chloroethyl)-morpholine hydrochloride (5.07 g, 27.2 mmol) and K2CO3 (3.76 g, 27.2 mmol). The solution was heated to 63° C. for 24 hours. Additional K2CO3 (1.25 g, 9.08 mmol) and 4-(2-chloroethyl)-morpholine hydrochloride (1.69 g, 9.08 mmol) was added and the mixture heated for an additional 24 hours at 63° C. The mixture was then partitioned between ethyl acetate and H2O, and the organic was washed with sat'd NaCl (3×30 mL) and dried over MgSO4. After concentration in vacuo, the residue was purified by flash chromatography (20:80 hexane/EtOAc) to afford N-[[4-[(3-methylphenyl)thio]phenyl]sulfonyl)-N-[2-(4-morpholinyl)ethyl]-D-valine, 1,1-dimethylethyl ester, as a white solid (5.21 g): MS MH+ calc'd for C28H41N2O5S2 : 549, found: 549. HRMS calc'd for C28H41N2O5S2 : 548.2379; found: 548.2384.

Provenance & Evidence