Sodium Methoxide → (2S,3R)-3-(4-Benzyloxy-2-methyl-phenyl)-2-ethoxy-3-hydroxy-propionic acid methyl ester

A 5.4 M solution of sodium methoxide (7.3 ml, 39.5 mmol) was added to an ice-cooled and stirred suspension of (S)-4-benzyl-3-[(2S,3R)-3-(4-benzyloxy-2-methyl-phenyl)-2-ethoxy-3-hydroxy-propionyl]-oxazolidin-2-one (17.6 g, 36 mmol) in dry methanol (87 ml). The mixture was stirred at 0° C. for 15 min, quenched and neutralized by the addition of dilute aqueous hydrochloric acid (1.0 M). The solution was concentrated under reduced pressure and the residue dissolved in ice water/ethyl acetate 1/1. The layers were separated and the aqueous layer was extracted two times with ethyl acetate. The combined organic layers were washed with ice water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, cyclohexane/AcOEt) to give 8.6 g (25 mmol, 69%) of the title compound as light yellow oil. According to 1H-NMR spectroscopy, one single diastereomer was obtained.

1. temperaturecooled
2. stirringThe mixture was stirred at 0° C. for 15 min
3. customquenched
4. additionneutralized by the addition of dilute aqueous hydrochloric acid (1.0 M)
5. concentrationThe solution was concentrated under reduced pressure
6. dissolutionthe residue dissolved in ice water/ethyl acetate 1/1
7. customThe layers were separated
8. extractionthe aqueous layer was extracted two times with ethyl acetate
9. washThe combined organic layers were washed with ice water
10. dry with materialdried over sodium sulfate
11. customThe solvent was removed under reduced pressure
12. customthe residue purified by column chromatography (silica gel, cyclohexane/AcOEt)

ORD record

ord-5cd29e44331142519ad68c4b91fdc4c6

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07348349B2