2-Methylbenzoyl chloride → 2'-deoxy-3',5'-di-O-acetyl-5-fluoro-3-(2-methylbenzoyl)uridine

HRID 745651Notes

Reaction equation

HRID 745651 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[NH:18][C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2].[CH3:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>N1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][C:12](=[O:14])[CH3:13])[O:8][C@@H:7]([N:15]2[CH:22]=[C:21]([F:23])[C:19](=[O:20])[N:18]([C:27](=[O:28])[C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[CH3:24])[C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 702762-Methylbenzoyl chlorideHCID 127901643',5'-Di-O-acetyl-2'-deoxy-5-fluorouridine

Product 1

HCID 131898962'-deoxy-3',5'-di-O-acetyl-5-fluoro-3-(2-methylbenzoyl)uridineYield 29.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

500 mg of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine was dissolved in 5 ml of dry pyridine, and the resulting solution was cooled with ice. To the solution was added 710 mg of 2-methylbenzoyl chloride, and the mixture was allowed to stand at room temperature for 100 minutes. The same procedure as in Example 1 gave 200 mg (yield: 29.5%) of 2'-deoxy-3',5'-di-O-acetyl-5-fluoro-3-(2-methylbenzoyl)uridine as crystals having a melting point of 108° to 109° C. This was identical with the crystals obtained in Example 1 by the mixed examination.

Workup

  1. temperaturethe resulting solution was cooled with ice

Sources & evidence

ORD record
ord-83d66a81bb8743d696e1c7e529bcb040
Source dataset
uspto-grants-1986_07
Patent number
US04599404

Reaction notes

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