Dicyclohexylcarbodiimide → 2',3'-Dideoxy-3'-fluoro-5'-O-[2-(N-FMOC-L-valyloxy)stearoyl] guanosine

HRID 1790829Notes

Reaction equation

HRID 1790829 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:37][C@H:38]([C:42]([O:44][CH:45]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[C:46](O)=[O:47])=[O:43])[CH:39]([CH3:41])[CH3:40])([O:22][CH2:23][CH:24]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:21].C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CN(C=O)C>[F:1][C@@H:2]1[C@@H:6]([CH2:7][O:8][C:46](=[O:47])[CH:45]([O:44][C:42](=[O:43])[C@H:38]([CH:39]([CH3:40])[CH3:41])[NH:37][C:20]([O:22][CH2:23][CH:24]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]3[C:25]2=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH3:64])[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

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 233875212-(N-FMOC-L-valyloxy)stearic acidHCID 1354318173'-Fluoro-2',3'-dideoxyguanosine

Product 1

HCID 1363776292',3'-Dideoxy-3'-fluoro-5'-O-[2-(N-FMOC-L-valyloxy)stearoyl] guanosine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2′,3′-dideoxy-3′-fluoroguanosine (404 mg, 1.5 mmole), 2-(N-FMOC-L-valyloxy)stearic acid (1.24 g, 2 mmole), DMAP (24 mg, 0.2 mmole) and HOBT (264 mg, 1,95 mmole) was coevaporated two times with DMF and reduced to about 30 ml. DCC (372 mg, 1.8 mmole) was added and the mixture was stirred overnight at room temperature. The mixture was filtered and the solution was evaporated under reduced pressure. Ethyl acetate (50 ml) was added and the organic phase washed twice with 5% acetic acid, with 5% sodium hydrogen carbonate and with water. The organic phase was dried with sodium sulfate and evaporated under reduced pressure.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solution was evaporated under reduced pressure
  3. additionEthyl acetate (50 ml) was added
  4. washthe organic phase washed twice with 5% acetic acid, with 5% sodium hydrogen carbonate and with water
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5c010298e2b44b96af3f510dd0f0351d
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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