2-hydroxy-3-methoxy-3,3-diphenylpropanoic acid → (2S)-2-Hydroxy-3-methoxy-3,3-diphenylpropanoic acid

Temperature

27.5 °C

R(+)-phenyl ethyl amine (11.12 grams) was added to a solution of 2-hydroxy-3-methoxy-3,3-diphenylpropionic acid (25 grams) and chloroform (25 ml) at 40° C. and stirred for 30 minutes. The reaction mixture was cooled, and the solid obtained was filtered and washed with chloroform. Ethyl acetate (50 ml) and water (50 ml) was added to the obtained solid and then the reaction mixture was acidified with concentrated hydrochloric acid. The layers were separated and the aqueous layer extracted with ethyl acetate. The solvent from combined organic layer was distilled off completely under reduced pressure at below 60° C. The obtained residue was dissolved in toluene (30 ml) at 60-70° C. and then cooled to 25-30° C. The solid was filtered, washed with toluene and then dried to get the title compound.

1. temperatureThe reaction mixture was cooled
2. customthe solid obtained
3. filtrationwas filtered
4. washwashed with chloroform
5. additionEthyl acetate (50 ml) and water (50 ml) was added to the obtained solid
6. customThe layers were separated
7. extractionthe aqueous layer extracted with ethyl acetate
8. distillationwas distilled off completely under reduced pressure at below 60° C
9. dissolutionThe obtained residue was dissolved in toluene (30 ml) at 60-70° C.
10. filtrationThe solid was filtered
11. washwashed with toluene
12. customdried

ORD record

ord-fdbede3c4a964a0e830c83ce6de18c5d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404840B2