Hydrochloric Acid → Cytarabine

HRID 1447703Notes

Reaction equation

HRID 1447703 reaction equation
[CH:1]1[C:15](=[NH:16])[N:14]=[C:13]2[N:3]([C@@H:4]3[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]3[O:12]2)[CH:2]=1.Cl.C[OH:19]>>[C@@H:4]1([N:3]2[CH:2]=[CH:1][C:15]([NH2:16])=[N:14][C:13]2=[O:12])[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]1[OH:19]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 25051Ancitabine

Product 1

HCID 6253Cytarabine

Procedure

A solution of the diacetyl derivative (30 mg.) of the carbocyclic analog of cyclocytidine, described immediately above, in methanol (15 ml.) saturated with hydrogen chloride was stirred at room temperature overnight. Evaporation of volatile components with a stream of nitrogen, then under reduced pressure, and in a high vacuum left the hydrochloride of the carbocyclic analog of cyclocytidine (30 mg.); the mass spectrum included the expected peaks (m/e 223, 206, 192). A solution of this material in 1 N aqueous ammonia (2 ml.) was heated at 80°-85° for 5 min. Volatile components were evaporated under reduced pressure and, then, in a high vacuum. Crystallization of the residue from ethanol gave the carbocyclic analog of 1-β-arabinofuranosylcytosine. This compound may also be isolated by ion-exchange chromatography, by preparative thin-layer chromatograhy, or by the sequential use of these techniques after impure preparations containing the carbocyclic analog of cyclocytidine are treated with aqueous ammonia. The properties of the pure compound prepared by the procedure of either Part A or Part B are summarized in Part A.

Workup

  1. customEvaporation of volatile components with a stream of nitrogen
  2. waitunder reduced pressure, and in a high vacuum left the hydrochloride of the carbocyclic analog of cyclocytidine (30 mg.)
  3. temperatureA solution of this material in 1 N aqueous ammonia (2 ml.) was heated at 80°-85° for 5 min
  4. customVolatile components were evaporated under reduced pressure
  5. customCrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-607682667cf3438b944f966153cb8b28
Source dataset
uspto-grants-1979_12
Patent number
US04177348

Reaction notes

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