Methanesulfonyl chloride →

Temperature

-50 °C

A solution of 5.00 g of N-trichloroethoxycarbonylglycine and 6.10 g of 4-(N,N-dimethylamino)pyridine dissolved in 35 ml of methylene chloride was cooled to -50° C. Thereinto was dropped 2.10 g of methanesulfonyl chloride. After the completion of the dropping, the resulting mixture was stirred at the same temperature for 1 hour. Thereinto was dropped 4.93 g of phytol at the same temperature, after which the temperature of the reaction mixture was elevated to room temperature in 6 hours. The reaction mixture was then washed with 2N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue obtained was dissolved in 86 ml of tetrahydrofuran. To the resulting solution were added 86 ml of 0.5N aqueous potassium primary phosphate solution and 13.40 g of zinc powder. The resulting mixture was stirred for 2 hours at room temperature. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. To the residue obtained was added 30 ml of ethyl acetate. The resulting mixture was washed with 2N hydrochloric acid and then dried over anhydrous magnesium sulfate. Into the resulting solution was introduced hydrogen chloride gas. Then, the solvent was removed from the resulting solution by distillation under reduced pressure to obtain 5.80 g (yield: 90%) of oily glycylphytyl hydrochloride.

1. waitafter which the temperature of the reaction mixture was elevated to room temperature in 6 hours
2. washThe reaction mixture was then washed with 2N hydrochloric acid, 3% aqueous sodium hydrogencarbonate solution and water in this order
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed by distillation under reduced pressure
5. customThe residue obtained
6. stirringThe resulting mixture was stirred for 2 hours at room temperature
7. filtrationThe reaction mixture was filtered
8. concentrationThe filtrate was concentrated under reduced pressure
9. customTo the residue obtained
10. washThe resulting mixture was washed with 2N hydrochloric acid
11. dry with materialdried over anhydrous magnesium sulfate
12. additionInto the resulting solution was introduced hydrogen chloride gas
13. customThen, the solvent was removed from the resulting solution by distillation under reduced pressure

ORD record

ord-0eb1676fe7814df3aa9bd3d77f9c240d

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05236950