Methyl iodide → HCID 15431767, compound

Temperature

0 °C

In a 500 mL flask equipped with magnetic stirrer, N-(t-butyloxycarbonyl)-(D)-phenylalaninol(0.040 mole, 10.05 g) was dissolved in 200 mL of THf and was added with NaH(0.048 mole, 1.15 g) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour, followed by the addition of CS2 (0.048 mole, 3.65 g). After being stirred for 40 min. at 0° C., MeI(0.048 mole, 6.81 g) was added to the reaction mixture. 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 11.3 g of O-thiocarbamoyl-N-(t-butyloxycarbonyl)-(D)-phenylalaninol: Yield 78%.

1. customIn a 500 mL flask equipped with magnetic stirrer
2. stirringAfter being stirred for 40 min. at 0° C.
3. stirringThe reaction mixture was stirred at room temperature for 2 hours
4. customThe resulting solution was quenched with water
5. extractionThe organic layer was extracted 3 times with dichloromethane
6. dry with materialdried over magnesium sulfate
7. distillationdistilled in vacuo
8. customto give a solid
9. customThis was recrystalized in a solution mixture of n-hexane and diethyl ether

ORD record

ord-a03109875335451089757cc5054e5449

Source dataset

uspto-grants-1999_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05935997