Dicyclohexylcarbodiimide → 2',3'-dideoxy-3'-fluoro-5'-O-{3-[2,3-bis(N-CBZ-L-valyloxy)-1-propyloxycarbonyl]propanoyl}guanosine

A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (0.538 g, 2 mmole), HOBT (0.327 g, 2.42 mmole), DMAP (29.3 mg, 0.24 mmole) and succinic acid 2,3-bis-(N-CBZ-L-valyloxy)-1-propyl ester (1.6 g, 2.42 mmole) was coevaporated two times with DMF and reduced to about 50 ml. DCC (0.536 g, 2.6 mmole) was added and the mixture was stirred 72 hours at room temperature. The mixture was filtered and the solution was evaporated under reduced pressure. 100 ml of ethyl acetate was added and the organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 0.65 g.

1. filtrationThe mixture was filtered
2. customthe solution was evaporated under reduced pressure
3. addition100 ml of ethyl acetate was added
4. washthe organic phase washed twice with 5% acetic acid, 5% sodium hydrogen carbonate and water
5. dry with materialThe organic phase was dried with sodium sulfate
6. customevaporated under reduced pressure
7. customThe product was isolated by silica gel column chromatography

ORD record

ord-1a9481b28f324096a84ef04565ca3e7c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07825238B2