Ethanol → Cytidine, N-benzoyl-2′-deoxy-5-[3-[(trifluoroacetyl)amino]-1-propenyl]-

HRID 1736631Notes

Reaction equation

HRID 1736631 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]([NH:5][CH2:6][CH:7]=[CH:8][C:9]1[C:10]([NH2:24])=[N:11][C:12](=[O:23])[N:13]([CH:22]=1)[C@@H:14]1[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]1)=[O:4].FC(F)(F)[C:29]([CH:31](N)[CH:32]=[CH:33][C:34]1[C:35](N)=NC(=O)N([CH:47]=1)[C@@H]1O[C@H](CO)[C@@H](O)C1)=O.C([OH:55])C>>[C:35]([NH:24][C:10]1[C:9]([CH:8]=[CH:7][CH2:6][NH:5][C:3](=[O:4])[C:2]([F:25])([F:1])[F:26])=[CH:22][N:13]([C@@H:14]2[O:21][C@H:18]([CH2:19][OH:20])[C@@H:16]([OH:17])[CH2:15]2)[C:12](=[O:23])[N:11]=1)(=[O:55])[C:34]1[CH:47]=[CH:29][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 54456449HCID 54456449, compoundHCID 67650911HCID 67650911, compound

Product 1

HCID 53746134Cytidine, N-benzoyl-2′-deoxy-5-[3-[(trifluoroacetyl)amino]-1-propenyl]-

Procedure

Repeating the nucleoside precursor synthesis procedure of Example I, but replacing 5-chloromercuri-2'-deoxyuridine with 5-chloromercuri-2'-deoxycytidine is productive of 5-(3-trifluoroacetylaminopropenyl)-2'-deoxycytidine (UV max 287 mn). Purified 5-(3-trifluoroacetyl-aminopropenyl)-2'-deoxycytidine (1.3 g, 4.6 mmol) is stirred in 80 ml anhydrous ethanol, benzoyl anhydride (1.5 g, 7 mmol) is added, and the reaction refluxed. Five additional 1.5 g portions of benzoyl anhydride are added hourly. After the reaction is judged complete by thin layer chromatography [silica plates eluting n-butanol/methanol/conc NH4OH/H2O (60:20:1:20)in 6-10 hours, the reaction is cooled and concentrated under reduced pressure to a semisolid. The solid is triturated with ether three times, decanted and dried. The crude product is crystallized from water to give chromatographically pure N4 -benzoyl-5-(3-trifluoroacetylaminopropenyl)-2'-deoxycytidine as a white solid. The product decomposes above 120° C.; UV λmax 311 nm.

Workup

  1. temperaturethe reaction refluxed
  2. washeluting n-butanol/methanol/conc NH4OH/H2O (60:20:1:20)in 6-10 hours
  3. temperaturethe reaction is cooled
  4. concentrationconcentrated under reduced pressure to a semisolid
  5. customThe solid is triturated with ether three times
  6. customdecanted
  7. customdried
  8. customThe crude product is crystallized from water

Sources & evidence

ORD record
ord-f7fcdc2c9c87459db310f227095f3392
Source dataset
uspto-grants-1996_07
Patent number
US05541313

Reaction notes

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