3-Pyridinecarbonyl chloride, hydrochloride (1:1) → 3'-(3-Pyridylcarbonyl)-5'-pivaloyltrifluorothymidine

HRID 359888Notes

Reaction equation

HRID 359888 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]=1

Participants

4

Reactant 2

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 131716752HCID 131716752, compound

Product 1

HCID 1317167533'-(3-Pyridylcarbonyl)-5'-pivaloyltrifluorothymidineYield 87.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 ##STR135## as further confirmed by NMR spectral analysis.

Workup

  1. temperaturecooling
  2. extractionextracted with 100 mL of ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customto give an oil
  7. customCrystallization from n-hexane

Sources & evidence

ORD record
ord-e0435a5c97b2412a956e31d3c1064fc3
Source dataset
uspto-grants-1991_03
Patent number
US05002935

Reaction notes

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