Palmitoyl chloride → 3'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

HRID 465302

Reaction equation

HRID 465302 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[F:19][C@@H:20]1[C@@H:24]([CH2:25][OH:26])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1.C(Cl)(Cl)Cl.CO>N1C=CC=CC=1>[F:19][C@@H:20]1[C@@H:24]([CH2:25][O:26][C:1](=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[O:23][C@@H:22]([N:27]2[CH:35]=[C:33]([CH3:34])[C:31](=[O:32])[NH:30][C:28]2=[O:29])[CH2:21]1

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 330393'-FluorothymidineHCID 21584188Chloroform methanol

Product 1

HCID 152283303'-deoxy-3'-fluoro-5'-O-palmitoyl-thymidine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

At 0° C., 1.2 equivalents of palmitoyl chloride are added to a solution of 3'-deoxy-3'-fluorothymidine in pyridine. The solution is warmed slowly to room temperature. As soon as a thin layer chromatographic control (CHCl3 /methanol=95/5 on silica gel) shows a complete reaction, the solution is poured into ice water. The aqueous phase is decanted, the resulting oil is chromatographed on silica gel with chloroform eluent. The title compound is recovered from the suitable fractions by evaporation of the solvent. M.P. 65°-66° C. (cyclohexane).

Workup

  1. customa complete reaction
  2. customThe aqueous phase is decanted
  3. customthe resulting oil is chromatographed on silica gel with chloroform eluent
  4. customThe title compound is recovered from the suitable fractions by evaporation of the solvent

Sources & evidence

ORD record
ord-6d05020b4ad54e78a4feb53e3d6ecd84
Source dataset
uspto-grants-1992_10
Patent number
US05153180

Linked notes

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