HCID 22339950, compound → HCID 22339947, compound

BH3-THF complex (15 mL of a 1.0 M solution in THF) was added dropwise via addition funnel over 50 min to a solution of [5-methyl-2-(5-methyl-thiophen-2-yl)-oxazol-4-yl]-acetic acid (1.5 g, 6.33 mmol) in THF (10 mL). The reaction mixture was stirred at ambient temperature for 3 h, and then quenched with MeOH (4 mL). After heating at 50° C. for 2 h, the reaction mixture was cooled to ambient temperature, and then partitioned between CH2Cl2 and 1N NaOH. The organic phase was washed with brine (1×50 mL), dried over MgSO4 and concentrated to obtain a colorless oil (1.4 g, 99%) which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=3.6 Hz, 1H), 6.73 (dd, J=3.6, 0.8 Hz, 1H), 3.89 (q, J=5.6 Hz, 2H), 3.04 (t, J=5.9 Hz, 1H), 2.68 (t, J=5.6 Hz, 2H), 2.51 (s, 3H), 2.30 (s, 3H); MS (EI+) 224.04 (M+H); 246.06 (M+H+Na).

1. customquenched with MeOH (4 mL)
2. temperatureAfter heating at 50° C. for 2 h
3. temperaturethe reaction mixture was cooled to ambient temperature
4. custompartitioned between CH2Cl2 and 1N NaOH
5. washThe organic phase was washed with brine (1×50 mL)
6. dry with materialdried over MgSO4
7. concentrationconcentrated

ORD record

ord-44b9bdf72f344a83bcd7c8fddbe5b92c

Source dataset

uspto-grants-2008_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07345070B2