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

HRID 703548Notes

Reaction equation

HRID 703548 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 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-6348199efce9494699bd22dd4158e889
Source dataset
uspto-grants-1991_01
Patent number
US04983609

Reaction notes

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