4-Methylmorpholine → N-[(S)-2,3-dihydroxypropionyl]-L-cysteine methyl ester

Temperature

20 °C

To a solution of 60.0 g of sodium-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]carboxylate in 500 ml of dimethylformamide were added 136.0 g of O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium-hexafluorophosphate. The mixture was stirred at 20° C. for 0.5 hours, then 62 g L-cysteine methyl ester hydrochloride and subsequently 36.7 g of N-methylmorpholine were added. The mixture was stirred at 20° C. for 3.5 hours. The solvent was evaporated in vacuo and the oily residue was partitioned between water and ethyl acetate. The organic layer was washed successively with saturated sodium carbonate solution, saturated potassium hydrogensulfate solution, and brine, and then dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residual oil was heated at reflux in a mixture of 50 ml of trifluoroacetic acid and 500 ml of methanol for 2.5 hours. The solvent was evaporated in vacuo, and the residue was crystallized from tert-butyl-methyl-ether to give 33.4 g of N-[(S)-2,3-dihydroxypropionyl]-L-cysteine methyl ester as white crystals of m.p. 90°-92° C.

1. stirringThe mixture was stirred at 20° C. for 3.5 hours
2. customThe solvent was evaporated in vacuo
3. customthe oily residue was partitioned between water and ethyl acetate
4. washThe organic layer was washed successively with saturated sodium carbonate solution, saturated potassium hydrogensulfate solution, and brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated in vacuo
7. temperaturethe residual oil was heated
8. temperatureat reflux in a mixture of 50 ml of trifluoroacetic acid and 500 ml of methanol for 2.5 hours
9. customThe solvent was evaporated in vacuo
10. customthe residue was crystallized from tert-butyl-methyl-ether

ORD record

ord-759bd8d4f8674924b4e1ef160a682b07

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05486466