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

HRID 1154526Notes

Reaction equation

HRID 1154526 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].C(N(CC)CC)C.CCOCC.[CH3:36][C:37]1[CH:45]=[CH:44][CH:43]=[CH:42][C:38]=1[C:39](Cl)=[O:40]>C(Cl)(Cl)Cl.CO>[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:39](=[O:40])[C:38]3[CH:42]=[CH:43][CH:44]=[CH:45][C:37]=3[CH3:36])[C:16]2=[O:17])[CH2:6]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 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)uridine

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

500 mg of 2'-deoxy-3',5'-di-O-acetyl-5-fluorouridine and 0.76 ml of triethylamine were added to 20 ml of dry ether, and the resulting mixture was stirred. To the mixture was added 710 mg of 2-methylbenzoyl chloride, and the resulting mixture was stirred at room temperature for 6 hours. The mixture was subjected to thin-layer chromatography on silica gel, together with the product in Example 1 as an authentic compound, using a mixed solvent of chloroform/methanol (39/1), thereby indicating that in the mixture was formed 2'-deoxy-3',5'-di-O-acetyl-5-fluoro-3-(2-methylbenzoyl)uridine. The Rf value was 0.62.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 6 hours

Sources & evidence

ORD record
ord-66d28934a0ee4a74a7c5e391b912d7e6
Source dataset
uspto-grants-1984_12
Patent number
US04490366

Reaction notes

Loading…