Hydrochloric Acid → 1-(2-O-nitro-beta-D-arabinofuranosyl)cytosine hydrochloride

HRID 1906366Notes

Reaction equation

HRID 1906366 reaction equation
[N+:1]([O:4][C@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[CH:20]=[CH:19][C:17]([NH2:18])=[N:16][C:14]1=[O:15])([O-:3])=[O:2].C(OCC)(=O)C.O.[ClH:28]>CO.C(O)CC>[ClH:28].[N+:1]([O:4][C@H:5]1[C@H:9]([OH:10])[C@@H:8]([CH2:11][OH:12])[O:7][C@H:6]1[N:13]1[CH:20]=[CH:19][C:17]([NH2:18])=[N:16][C:14]1=[O:15])([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 1343641-(2-O-Nitro-beta-D-arabinofuranosyl)cytosine

Product 1

HCID 704284171-(2-O-nitro-beta-D-arabinofuranosyl)cytosine hydrochlorideYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10311-PropanolSolvent

Procedure

A solution of 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine [6.6 g., 23 mmol. which was a white foam that was homogeneous by TLC (upper phase of 4:2:1=ethyl acetate:H2O:1-propanol)] in methanol was acidified with concentrated hydrochloric acid until the pH of the solution was ~1.0. A white solid began to separate immediately. The solvent was removed under reduced pressure, and the resulting residue was coevaporated with methanol (3×200 ml). The product thus obtained was dried in vacuo and crystallized from a mixture of 1:1=absolute ethanol: 96% ethanol. The crystals were collected by centrifugation to obtain pure 1-(2-O-nitro-β-D-arabinofuranosyl)cytosine hydrochloride (4.83 g., 65%): m.p.>170° C. dec. The salt had these physical characteristics:

Workup

  1. customto separate immediately
  2. customThe solvent was removed under reduced pressure
  3. customThe product thus obtained
  4. customwas dried in vacuo
  5. customcrystallized from a mixture of 1:1=absolute ethanol
  6. customThe crystals were collected by centrifugation

Sources & evidence

ORD record
ord-5d6cd6de83c046e0ad6303d3406c4f56
Source dataset
uspto-grants-1987_03
Patent number
US04652554

Reaction notes

Loading…