Dicyclohexylcarbodiimide → 5'-(N-CBz-L-valyl)-2',3'-dideoxy-3'-fluoroguanosine

HRID 489080Notes

Reaction equation

HRID 489080 reaction equation
[F:1][C@@H:2]1[C@@H:6]([CH2:7][OH:8])[O:5][C@@H:4]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[CH2:3]1.[C:20]([NH:30][C@H:31]([C:35](O)=[O:36])[CH:32]([CH3:34])[CH3:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:20]([NH:30][C@H:31]([C:35]([CH:7]([OH:8])[C@H:6]1[O:5][C@@H:4]([N:9]2[C:19]3[N:18]=[C:16]([NH2:17])[NH:15][C:13](=[O:14])[C:12]=3[N:11]=[CH:10]2)[CH2:3][C@@H:2]1[F:1])=[O:36])[CH:32]([CH3:34])[CH3:33])([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21]

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 726987N-Carbobenzoxy-L-valineHCID 1354318173'-Fluoro-2',3'-dideoxyguanosine

Product 1

HCID 1363356555'-(N-CBz-L-valyl)-2',3'-dideoxy-3'-fluoroguanosine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2′,3′-dideoxy-3′-fluoroguanosine (810 mg, 3 mmole) and 4-dimethylaminopyridine (73 mg, 0.6 mmole), N-CBz-L-valine (1.5 g, 6 mmole) and 1-hydroxybenzotriazole (810 mg, 6 mmole) in DMF (20 ml) was added DCC (1.36 g, 6.6 mmole). After 72 h, the reaction mixture was filtered and concentrated in vacuo. 5′-(N-CBz-L-valyl)-2′,3′-dideoxy-3′-fluoroguanosine was isolated by silica gel column chromatography (1.15 g).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c486dc7bdd94a0eb5d47774ad77bc67
Source dataset
uspto-grants-2005_12
Patent number
US06974802B2

Reaction notes

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