Water → Cytarabine

HRID 976094Notes

Reaction equation

HRID 976094 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(N)(C)(C)C.[OH2:23]>>[CH:1]1[C:15]([NH2:16])=[N:14][C:13](=[O:12])[N:3]([C@@H:4]2[O:8][C@H:7]([CH2:9][OH:10])[C@@H:6]([OH:11])[C@@H:5]2[OH:23])[CH:2]=1

Participants

4

Reactant 3

HCID 962WaterHCID 6385Tert-ButylamineHCID 2505010212-25-6

Product 1

HCID 6253CytarabineYield 83%

Procedure

2,2'-O-cyclocytidine hydrochloride (6.5 g) was dissolved in 35 mL water at 80° C. The solution was cooled to room temperature and t-butylarnine (2.8 g) was added and the mixture stirred for 2 hours. Thereafter, the solvent was evaporated under vacuum and ethanol (16 g) was added. The mixture was stirred at room temperature for 12 hours. Filtration of the resulting precipitation yielded 5 g of pure cytarabine after drying, which corresponds to a yield of 83%. The product was characterized by comparison of its melting point, and NMR and IR spectra with those previously reported for cytarabine.

Workup

  1. customThereafter, the solvent was evaporated under vacuum and ethanol (16 g)
  2. additionwas added
  3. stirringThe mixture was stirred at room temperature for 12 hours
  4. filtrationFiltration of the resulting precipitation

Sources & evidence

ORD record
ord-305e6519f328428f83edefa32a2e0332
Source dataset
uspto-grants-1997_03
Patent number
US05610292

Reaction notes

Loading…