Hexamethyldisilazane → HCID 59468964, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (5R)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-5-[4-{[(2-fluorophenyl)methyl]oxy}-3-(methyloxy)phenyl]-2-methyl-L-proline (D60, 150 mg, 0.33 mmol), diisopropylethyl amine (0.115 ml, 0.66 mmol) and TBTU (116 mg, 0.36 mmol) in dry DMF (5 ml) was stirred for 15 min at room temperature. HMDS (0.106 ml, 0.5 mmol) was added and stirring was continued at room temperature for 2 h. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added and the resulting suspension was stirred for 30 min. The mixture was extracted with ethyl acetate and washed three times with ice cold brine. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by chromatography on silica gel using cyclohexane and ethyl acetate (8:2 to 7:3) to afford the title compound (110 mg, 73%); Rt (HPLC): 5.68 min; MS: (ES/+) m/z: 481 [M+Na] C25H31FN2O5 requires 458.

Provenance & Evidence