Imidazole → HCID 18443667, compound

To a solution of 3-(4-hydroxy-3-methoxy-phenyl)-2-methoxy-propionic acid (1.02 g, 4.87 mmol) in CH2Cl2-DMF (20 mL=10:1) was added tert-butyl-dimethylsilyl chloride (1.75 g, 11.68 mmol) and imidazole (0.70 g, 10.24 mmol). The resulting solution was stirred at room temperature overnight. Water (15 mL) was added, and the aqueous phase was extracted with hexanes (30 mL). The hexanes layer was washed with water (10 mL), dried (MgSO4), filtered, and concentrated. The crude product was dissolved in ethyl acetate (10 mL), and a saturated solution of K2CO3 (5 mL) was added. The resulting mixture was stirred for 2 hours at room temperature. The aqueous layer was extracted with ethyl acetate (10 mL), acidified to pH 3, and extracted again with ethyl acetate (3×10 mL). The later organic layers were combined and washed with brine (20 mL), dried (MgSO4), and concentrated to a yellow oil (1.2 g, 77%). 1H-NMR (200.15 MHz, CDCl3): δ 6.78–6.67 (m, 3H), 3.96 (dd, 1H, J=7.8, 4.0), 3.78 (s, 3H), 3.35 (s, 3H), 3.09 (dd, 1H, J=14.2, 4.0), 2.91 (dd, 1H, J=14.2, 7.8), 0.98 (s, 9H), 0.13 (6H, s).

1. extractionthe aqueous phase was extracted with hexanes (30 mL)
2. washThe hexanes layer was washed with water (10 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe crude product was dissolved in ethyl acetate (10 mL)
7. additiona saturated solution of K2CO3 (5 mL) was added
8. stirringThe resulting mixture was stirred for 2 hours at room temperature
9. extractionThe aqueous layer was extracted with ethyl acetate (10 mL)
10. extractionextracted again with ethyl acetate (3×10 mL)
11. washwashed with brine (20 mL)
12. dry with materialdried (MgSO4)
13. concentrationconcentrated to a yellow oil (1.2 g, 77%)

ORD record

ord-a64ad25010ce46608f4c9e20881edca7

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192982B2