Acetic Acid → 2',3'-Dideoxy-3'-fluoro-5'-O-[2-(L-valyloxy) stearoyl]guanosine
Reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:52])[CH:10]([O:27][C:28](=[O:51])[C@H:29]([CH:48]([CH3:50])[CH3:49])[NH:30]C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[O:5][C@@H:4]([N:53]2[C:63]3[N:62]=[C:60]([NH2:61])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]2)[CH2:3]1.C1CCN2C(=NCCC2)CC1.C(O)(=O)C>CN(C=O)C>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:9](=[O:52])[CH:10]([O:27][C:28](=[O:51])[C@H:29]([CH:48]([CH3:50])[CH3:49])[NH2:30])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[O:5][C@@H:4]([N:53]2[C:63]3[N:62]=[C:60]([NH2:61])[NH:59][C:57](=[O:58])[C:56]=3[N:55]=[CH:54]2)[CH2:3]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2′,3′-dideoxy-3′-fluoro-5′-O-[2-(N-FMOC-L-valyloxy) stearoyl]guanosine (800 mg, 0.89 mmole) in 15 ml DMF was added DBU (1.35 g, 8.9 mmole) and the mixture was stirred for 5 minutes at room temperature. Acetic acid (2 ml) was added and the mixture was evaporated under reduced pressure. Water (20 ml) were added and the mixture was extracted three times with dichloromethane. The organic phase was dried with sodium sulfate and evaporated under reduced pressure. The product was isolated by silica gel column chromatography. Yield: 165 mg
Workup
- customthe mixture was evaporated under reduced pressure
- additionWater (20 ml) were added
- extractionthe mixture was extracted three times with dichloromethane
- dry with materialThe organic phase was dried with sodium sulfate
- customevaporated under reduced pressure
- customThe product was isolated by silica gel column chromatography
Sources & evidence
- ORD record
- ord-81b0e4722d2a42798ccc195bb1527717
- Source dataset
- uspto-grants-2005_12
- Patent number
- US06974802B2
Reaction notes
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