3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 3'-(3-Pyridylcarbonyl)-5'-pivaloyltrifluorothymidine
Reaction equation
[C:1]([CH:7]([OH:26])[C@H:8]1[O:12][C@@H:11]([N:13]2[CH:24]=[C:19]([C:20]([F:23])([F:22])[F:21])[C:17](=[O:18])[NH:16][C:14]2=[O:15])[CH2:10][C@@H:9]1[OH:25])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].Cl.[C:28](Cl)(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[N:31][CH:30]=1>N1C=CC=CC=1>[N:31]1[CH:32]=[CH:33][CH:34]=[C:29]([C:28]([C@@:9]2([OH:25])[C@@H:8]([CH:7]([C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])[OH:26])[O:12][C@@H:11]([N:13]3[CH:24]=[C:19]([C:20]([F:21])([F:22])[F:23])[C:17](=[O:18])[NH:16][C:14]3=[O:15])[CH2:10]2)=[O:35])[CH:30]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of 450 mg of 5'-pivaloyltrifluorothymidine in 10 mL of pyridine was added 1.0 g of nicotinoyl chloride hydrochloride under ice-cooling. The reaction mixture was stirred at room temperature for 3 days, then was poured into 100 mL of ice water and extracted with 100 mL of ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate and then evaporated in vacuo to give an oil. Crystallization from n-hexane afforded 500 mg (87%) of colorless needles melting at 175°-177° C. The product had the structure ##STR134## as further confirmed by NMR spectral analysis.