Thymidine → HCID 67747744, compound

HRID 374079Notes

Reaction equation

HRID 374079 reaction equation
[C@@H:1]1([N:9]2[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1>N1C=CC=CC=1>[Cl:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([CH:6]([OH:7])[C@H:5]2[O:8][C@@H:1]([N:9]3[CH:17]=[C:15]([CH3:16])[C:13](=[O:14])[NH:12][C:10]3=[O:11])[CH2:2][C@@H:3]2[OH:4])=[O:24])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 5789ThymidineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 67747744HCID 67747744, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Reaction of thymidine with 4-chlorobenzoyl chloride in pyridine at 5° to 20° C. forms 5'-(4-chlorobenzoyl)thymidine (yield: 80%), which is then allowed to react with diethylaminosulfur trifluoride in methylene chloride at -78° C., thus giving 3'-deoxy-3'-fluorothymidine (yield: 19.9%) [Japanese Patent Kokai No. 68325 (1989)].

Sources & evidence

ORD record
ord-9a679509eacf459286da4af20671e6ac
Source dataset
uspto-grants-1992_11
Patent number
US05166327

Reaction notes

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