Water → HCID 11789773, compound

To a mixture of (2S,3R)-methyl-2-chloro-3-hydroxy phenylpropionate (CV, EXAMPLE 4, 31.6 g, 0.15 mol) in DMF (730 ml) is added water (13.5 ml) followed by potassium carbonate (62 g, 0.45 mol) at 25° with stirring. The mixture is allowed to stir at 25° for 72 hr and then poured into a mixture of ethyl acetate (3 l) and water (500 ml). The organic phase is separated and the aqueous phase is back washed with ethyl acetate (400 ml×2). The combined organic phases are washed with water (400 ml×3). The aqueous phases are extracted with ethyl acetate (100 ml). The combined organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to about 800 ml, the organic mixture is again washed with water (250 ml×4). The organic phase is dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to give the title compound, [α]25D=+15.0° (c=1.52, chloroform); NMR (300 MHz, CDCl3) 7.45-7.33, 4.30, 3.88 and 3.58 δ; CMR (300 MHz, CDCl3) 167.0, 132.7, 128.5, 128.0, 126.5, 57.5, 55.8 and 52.0 δ; MS (m/z) 178 (M+), 161, 131, 107, 105, 91, 79, 77 and 51.

1. stirringto stir at 25° for 72 hr
2. customThe organic phase is separated
3. washthe aqueous phase is back washed with ethyl acetate (400 ml×2)
4. washThe combined organic phases are washed with water (400 ml×3)
5. extractionThe aqueous phases are extracted with ethyl acetate (100 ml)
6. dry with materialThe combined organic phase is dried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure to about 800 ml
9. washthe organic mixture is again washed with water (250 ml×4)
10. dry with materialThe organic phase is dried over magnesium sulfate
11. filtrationfiltered
12. customthe solvent removed under reduced pressure

ORD record

ord-5e380ab6256c4517a21edce739651092

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06307064B1