Chloroacetic anhydride → 3'-O-benzyl-5'-O-chloroacetyl-2'-deoxy-5-fluorouridine

HRID 466091Notes

Reaction equation

HRID 466091 reaction equation
Cl[CH2:2][C:3]([O:5][C:6](=[O:9])[CH2:7][Cl:8])=O.[CH2:10]([O:17][C@@H:18]1[C@@H](CO)[O:21][C@@H:20]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:19]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:10]([O:17][C@@H:18]1[C@@H:2]([CH2:3][O:5][C:6](=[O:9])[CH2:7][Cl:8])[O:21][C@@H:20]([N:25]2[CH:32]=[C:31]([F:33])[C:29](=[O:30])[NH:28][C:26]2=[O:27])[CH2:19]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 10946Chloroacetic anhydrideHCID 10664574Uridine, 2'-deoxy-5-fluoro-3'-O-(phenylmethyl)-

Product 1

HCID 137150893'-O-benzyl-5'-O-chloroacetyl-2'-deoxy-5-fluorouridineYield 45%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Chloroacetic anhydride was added to a solution of 0.20 g of 3'-O-benzyl-2'-deoxy-5-fluorouridine in 10 ml of pyridine, and the mixture was left to stand at room temperature overnight. Then the same subsequent procedures as in Reference Example 54 were conducted, giving 0.11 g of the title compound as an oil in a yield of 45%.

Workup

  1. waitthe mixture was left

Sources & evidence

ORD record
ord-57beb9c9f2e545fcbeda93ad0b45458f
Source dataset
uspto-grants-1992_10
Patent number
US05155113

Reaction notes

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