Methyl iodide → HCID 11197673, compound

Participants

Reaction Conditions

Reaction Steps

In a 500 mL flask equipped with magnetic stirrer, N-(t-butyloxycarbonyl)-(DL)-phenylalaninol(0.051 mole, 13.6 g) was dissolved in 200 mL of THF and was added with NaH(0.061 mole, 1.47 g) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour, followed by the addition of CS2 (0.061 mole, 4.66 g). After being stirred for 40 min. at 0° C., MeI(0.061 mole, 8.69 g) was added to the reaction mnixture. The reaction mixture was stirred at room temperature for 2 hours, followed by the addition of 5N NH4OH (0.090 mole, 18.0 mL) for 6 hours. The resulting solution was quenched with water. The organic layer was extracted 3 times with dichloromethane, dried over magnesium sulfate and distilled in vacuo, to give a solid. This was recrystalized in a solution mixture-of n-hexane and diethyl ether, to produce 14.7 g of O-thiocarbamoyl-N-(t-butyloxycarbonyl)-(DL)-phenylalaninol: Yield 80%.

Provenance & Evidence