Benzoyl chloride → N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5-fluorocytidine

HRID 1089420Notes

Reaction equation

HRID 1089420 reaction equation
[F:1][C:2]1[C:3]([NH2:17])=[N:4][C:5](=[O:16])[N:6]([CH:15]=1)[C@@H:7]1[O:14][C@H:12]([CH3:13])[C@@H:10]([OH:11])[C@H:8]1[OH:9].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]([NH:17][C:3]1[C:2]([F:1])=[CH:15][N:6]([C@@H:7]2[O:14][C@H:12]([CH3:13])[C@@H:10]([O:11][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:8]2[O:9][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5](=[O:16])[N:4]=1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 100374995'-Deoxy-5-fluorocytidine

Product 1

HCID 53982579N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5-fluorocytidine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

5'-Deoxy-5-fluorocytidine (245 mg), benzoyl chloride (400 μl) and 4-dimethylaminopyridine (122 mg) were dissolved in dry pyridine (5 ml). After stirring for 3 hours at room temperature pyridine was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from methanol to give N4,2'-O,3'-O-tribenzoyl-5'-deoxy-5-fluorocytidine (280 mg), mp 158°~160° C.; MS 558 (MH+).

Workup

  1. customwas removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-6f80ff6256fc479cad8ec2f262acf0a0
Source dataset
uspto-grants-1990_10
Patent number
US04966891

Reaction notes

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