Dimethylformamide → Methyl (2S)-2-(phenylmethoxy)propanoate

Temperature

5 °C

Dimethyl formamide (0.5 ml) was added to a mixture of (S)-1-phenylethanamine salt of (S)-2-(benzyloxy)propanoic acid compound of formula-13a obtained in step-c) of above examples-9 &. 10 (200 g) and methanol (600 ml) and the reaction mixture was cooled to 0-5° C. Thionyl chloride (58.4 ml) was slowly added to the reaction mixture at 0-5° C. over a period of 1 hour and stirred for 1 hour at 0-10° C. After completion of the reaction, the reaction mixture was quenched with water and extracted with dichloro methane. Both aqueous and dichloro methane layers were separated, dichloro methane layer was washed with 10% sodium chloride and water. Distilled off the solvent completely from dichloro methane layer to get title compound. Yield: 129 g; Chiral purity: 99.5%

1. customof formula-13a obtained in step-c) of above examples-9
2. customAfter completion of the reaction
3. customthe reaction mixture was quenched with water
4. extractionextracted with dichloro methane
5. customBoth aqueous and dichloro methane layers were separated
6. washdichloro methane layer was washed with 10% sodium chloride and water
7. distillationDistilled off the solvent completely from dichloro methane layer

ORD record

ord-50e689c32cef4532880ec34193b55ae6

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102664B2