Nitric Acid → HCID 178440254, compound

Temperature

25 °C

Compound 4 (20 mg) was suspended in a mixture of concentrated sulfuric acid (1 mL) and chloroform (1 mL). To the resulting mixture, fuming nitric acid (166 μL: d=1.50) was added while being stirred and cooled with ice at 5° C. or below. The resulting mixture was allowed to slowly warm to room temperature (20-30° C.), and subsequently kept stirred at room temperature (20-30° C.) overnight. The reaction mixture was poured into ice and neutralized with a 10N aqueous sodium hydroxide solution to a pH of approx. 5 (at 20° C. or below). The mixture was extracted twice with chloroform and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methylene chloride: methanol=50:1 to 10:1) to give 17.8 mg (49% yield) of the desired product as a brown amorphous.

1. temperaturecooled with ice at 5° C. or below
2. stirringsubsequently kept stirred at room temperature (20-30° C.) overnight
3. additionThe reaction mixture was poured into ice
4. extractionThe mixture was extracted twice with chloroform
5. concentrationthe organic layer was concentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride: methanol=50:1 to 10:1)

ORD record

ord-98dffaeecf7a4a3994b879e6ba0392b7

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685989B2