Acetonitrile → HCID 51357517, compound

Solid 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5; 200 mg, 0.65 mmol) was added to a stirred suspension of CDI (106 mg, 0.65 mmol) in tetrahydrofuran (10 ml) under nitrogen at 20° C. The reaction mixture was stirred at room temperature for 10 min. 1,3-Oxazol-2-amine (54.7 mg, 0.65 mmol) was then added and the reaction mixture was refluxed overnight. The reaction mixture was concentrated. Water (100 ml) was added to the residue followed by extraction with ethyl acetate (3×50 ml). The combined organic phase was washed with saturated brine (25 ml), dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by thin layer chromatography (petroleum ether:ethyl acetate=2:1) followed by Prep-HPLC (Gilson GX-281; Shimazu 15 μm; 250*19 mm; A: 10 mmol NH4HCO3/water, B: CH3CN; 0-9 min, 70-80%; 9-9.3 min, 80-95%; 9.3-13 min, 95% CH3CN; RT: 8.0 min) to yield the title compound as a white solid. 15 mg.

1. temperaturethe reaction mixture was refluxed overnight
2. concentrationThe reaction mixture was concentrated
3. additionWater (100 ml) was added to the residue
4. extractionfollowed by extraction with ethyl acetate (3×50 ml)
5. washThe combined organic phase was washed with saturated brine (25 ml)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe crude product was purified by thin layer chromatography (petroleum ether:ethyl acetate=2:1)
9. custom0-9 min, 70-80%
10. custom9-9.3 min, 80-95%

ORD record

ord-cae7f56f128445ee82d13a12e988297a

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778939B2