Triphenylphosphine → Methyl (R)-(+)-3-(Acetylthio)-2-methylpropionate

Temperatur

0 °C

To a solution of (S)-( +)-3-hydroxy-2-methylpropionic acid methyl ester (8.00 g) and triphenyl phosphin (26.64 g) in tetrahydrofuran (170 ml) was added azodicarboxylic acid diethyl ester (16 ml) was added, followed by stirring at 0° C. for 30 minutes. After addition of thioacetic acid at 0° C., the reaction mixture was stirred at room temperature for 16 hours, after which saturated aqueous solution of sodium hydrogen carbonate was added and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was washed with hexane and the flitrate was concentrated. The resulting residue was distilled (83-87° C./0.2 mmHg) to yield the title compound (4.95 g, yield 41%) as a colorless oily substance.

1. additionwas added
2. stirringthe reaction mixture was stirred at room temperature for 16 hours
3. extractionthe reaction mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated saline
5. dry with materialdried over anhydrous sodium sulfate
6. distillationthe solvent was distilled off
7. washThe resulting residue was washed with hexane
8. concentrationthe flitrate was concentrated
9. distillationThe resulting residue was distilled (83-87° C./0.2 mmHg)

ORD-Eintrag

ord-c6d8c2dd889d438694f357733feb33c3

Quelldatensatz

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05506267