Methanol → HCID 68490295, compound

The product of Step (b) (72 mg, 0.15 mmol) in 96% formic acid (2 ml) was stirred at room temperature under nitrogen for 17 hours. Methanol was added and the mixture was evaporated in vacuo. The residue was dissolved in a small volume of water (10 ml), basified with saturated potassium carbonate solution and extracted with dichloromethane (10 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo. This residue was dissolved in dichloromethane (2 ml) under nitrogen and triethylamine (0.029 ml, 0.21 mmol) and methanesulfonyl chloride (0.016 ml, 0.21 mmol) were added sequentially. The resulting mixture was stirred at room temperature for 40 hours and then partitioned between dichloromethane (10 ml) and water (10 ml). The aqueous layer was separated and re-extracted with dichloromethane and the combined organic extracts were dried (MgSO4) and evaporated in vacuo. The residue was purified by flash chromatography, eluting with 40% ethyl acetate in iso hexane to give the title compound as a white solid (37 mg, 58%).

1. customthe mixture was evaporated in vacuo
2. dissolutionThe residue was dissolved in a small volume of water (10 ml)
3. extractionextracted with dichloromethane (10 ml)
4. dry with materialThe combined organic extracts were dried (MgSO4)
5. customevaporated in vacuo
6. dissolutionThis residue was dissolved in dichloromethane (2 ml) under nitrogen
7. custompartitioned between dichloromethane (10 ml) and water (10 ml)
8. customThe aqueous layer was separated
9. extractionre-extracted with dichloromethane
10. dry with materialthe combined organic extracts were dried (MgSO4)
11. customevaporated in vacuo
12. customThe residue was purified by flash chromatography
13. washeluting with 40% ethyl acetate in iso hexane

ORD record

ord-8f26752cf9dc452c8bc6155c34ad1b77

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07161006B2