Methyl iodide → HCID 86718363, compound

Participants

Reaction Conditions

Reaction Steps

NaH (42 mg, 1.0 mmol, 3.3 equiv) was added in 4 portions to a solution of (S)-2-Benzyloxycarbonylamino-4-methoxy-3-methoxymethyl-butyric acid (100 mg, 0.32 mmol, 1.0 equiv) in dry THF 1 mL at 0° C. After stirring at 0° C. for 10 minutes, it was added a solution of MeI (137 mg, 0.964 mmol, 3.0 equiv) in DMF/THF solution. The mixture was stirred at 0° C. for 1 hour then at room temperature for 16 hours. The reaction mixture was then added to saturated aqueous NH4Cl solution at 0° C. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give product 2.11b (100 mg, 95% yield). The crude material was continued to the next step with no further purification. MS m/z (M+1) 326.3

Provenance & Evidence