Hexamethyldisilazane → HCID 59468965, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (5R)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-2-methyl-5-{4-[(phenylmethyl)oxy]phenyl}-L-proline (D8, 870 mg, 2.11 mmol), diisopropylethyl amine (0.74 ml, 4.22 mmol) and TBTU (814 mg, 2.53 mmol) in dry DMF (8 ml) was stirred for 15 min at room temperature. HMDS (0.70 ml, 3.17 mmol) was added and stirring was continued at room temperature overnight. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 solution was added. 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 (7:3) to afford the title compound (857 mg, 99%); Rt (HPLC): 5.85 min; MS: (ES/+) m/z: 433 [M+Na+]; C24H30N2O4 requires 410; Rf (cyclohexane:ethyl acetate=6:4): 0.32.

Provenance & Evidence