Sodium Bicarbonate → HCID 66862768, compound

Temperature

65 °C

A mixture of Pt/C (10%, 15 g (20-30% mol equiv.) as a water slurry) and NaHCO3 (1.5 g, 17.94 mmol) in H2O (500 mL) was stirred at 65° C. under H, for 0.5 h. The reaction mixture was then allowed to cool, placed under a vacuum and flushed with N2 several times to completely remove all H2. Compound 4 (5.1 g, 17.94 mmol) was then added at room temperature. The reaction mixture was stirred at 65° C. under O2 (balloon) until the reaction was complete by LC-MS (typically 24-72 h). The mixture was cooled to room temperature and filtered. The Pt/C was washed with H2O extensively. The combined filtrates were concentrated to ˜30 mL, and acidified (pH 4) by the addition of HCl (4N) at 0° C. A black solid precipitated out which was collected by filtration. The crude product was dissolved in a minimum amount of Methanol and filtered through a pad of silica gel (eluting with Methanol). The filtrate was concentrated and crystallized from water to give compound 5 (2.5 g) as an off-white solid.

1. temperatureto cool
2. customflushed with N2 several times
3. customto completely remove all H2
4. stirringThe reaction mixture was stirred at 65° C. under O2 (balloon) until the reaction
5. customtypically 24-72 h
6. temperatureThe mixture was cooled to room temperature
7. filtrationfiltered
8. washThe Pt/C was washed with H2O extensively
9. concentrationThe combined filtrates were concentrated to ˜30 mL
10. additionby the addition of HCl (4N) at 0° C
11. customA black solid precipitated out which
12. filtrationwas collected by filtration
13. dissolutionThe crude product was dissolved in a minimum amount of Methanol
14. filtrationfiltered through a pad of silica gel (eluting with Methanol)
15. concentrationThe filtrate was concentrated
16. customcrystallized from water

ORD record

ord-a0164b131d484fdcb281d07a31c52c9c

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318701B2