Water → HCID 11856841, compound

The 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-[2-(2-methylallyl)phenyl]-2H-isoquinolin-1-one (25 mg, 0.064 mmol) obtained in Example 2-40 was dissolved in THF-water (3 ml-1 ml). Thereafter, an osmium oxide aqueous solution (0.1 mmol/ml, 0.032 ml, 0.0032 mmol) and sodium periodate (55 mg, 0.26 mmol) were added to the solution, and the obtained mixture was then stirred at a room temperature for 15 hours. Thereafter, water was added to the reaction mixture, followed by extraction with methylene chloride. The extract was dried over magnesium sulfate, and was then concentrated under reduced pressure. The thus obtained ketone body (24 mg) that was a roughly purified product was dissolved in methanol (2 ml) without being further purified. Thereafter, sodium borohydride (7.3 mg, 0.19 mmol) was added to the obtained solution under cooling on ice. The obtained mixture was stirred at a room temperature for 2 hours. Thereafter, the reaction solution was concentrated, and was then purified by preparative TLC (methylene chloride:methanol=10:1), so as to obtain 7-((R)-5-hydroxymethyl-2-oxooxazolidin-3-yl)-3-[2-(2-hydroxypropyl)phenyl]-2H-isoquinolin-1-one (15.3 mg, 61%, two-stage) in the form of white powders.

1. extractionfollowed by extraction with methylene chloride
2. dry with materialThe extract was dried over magnesium sulfate
3. concentrationwas then concentrated under reduced pressure
4. dissolutionwas dissolved in methanol (2 ml)
5. temperatureunder cooling on ice
6. stirringThe obtained mixture was stirred at a room temperature for 2 hours
7. concentrationThereafter, the reaction solution was concentrated
8. customwas then purified by preparative TLC (methylene chloride:methanol=10:1)

ORD record

ord-4459653b803a4ce8bd15e7f068973a8a

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07820693B2