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

HRID 1088909

Reaction equation

HRID 1088909 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 were added to a solution of 3'-deoxy-3'-fluorothymidine in pyridine. The solution was warmed slowly to room temperature. As soon as a thin layer chromatographic control (CHCl3 /methanol=95/5 on silica gel) showed a complete reaction, the solution was poured into ice water. The aqueous phase was decanted, the resulting oil was chromatographed on silica gel with chloroform eluent. The title compound was 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 was decanted
  3. customthe resulting oil was chromatographed on silica gel with chloroform eluent
  4. customThe title compound was recovered from the suitable fractions by evaporation of the solvent

Sources & evidence

ORD record
ord-3deb81ccc9e241bb87d8dc9f1e866483
Source dataset
uspto-grants-1990_10
Patent number
US04963662

Linked notes

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