Water → Uracil

HRID 25468

Reaction equation

HRID 25468 reaction equation
O.[NH:2]1[CH:9]=[CH:8][C:6](N)=[N:5][C:3]1=[O:4].[OH-].[Mg+2].[OH-].[C@@H:13]1([N:21]2[CH:28]=[CH:27][C:25](N)=[N:24][C:22]2=[O:23])[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1>C(O)(=O)C.C1CCCCC1>[NH:2]1[CH:9]=[CH:8][C:6](=[O:16])[NH:5][C:3]1=[O:4].[C@@H:13]1([N:21]2[CH:28]=[CH:27][C:25](=[O:4])[NH:24][C:22]2=[O:23])[O:20][C@H:17]([CH2:18][OH:19])[C@@H:15]([OH:16])[CH2:14]1

Participants

8

Reactant 4

HCID 962WaterHCID 13711DeoxycytidineHCID 73981Magnesium HydroxideHCID 178418229Cytosine4×

Product 2

HCID 1174UracilHCID 13712Deoxyuridine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8078CyclohexaneSolvent

Procedure

To the mixture of water (96.4 g) and 4.8 g of cyclohexane, were added 6.96 g (62.6 mmol) of cytosine, 18.7 g (75.4 mmol) of 2′-deoxyribose-1-phosphate diammonium salt, 7.58 g (132 mmol) of magnesium hydroxide and the frozen cell mass (2.0 g) prepared in Reference Example 3. The reaction took place at 45° C. for 18 hours, controlling the solution at pH 8.8 with acetic acid. The HPLC analysis after the reaction demonstrated that 10.03 g (70.5 mol %/cytosine) of 2′-deoxycytidine was produced as object compound. At the same time, 0.73 g (10.4 mol %/cytosine) of uracil and 1.80 g (12.6 mol %/cytosine) of 2′-deoxyuridine were produced as byproduct, respectively.

Workup

  1. customthe frozen cell mass (2.0 g) prepared in Reference Example 3
  2. customat 45° C.
  3. customfor 18 hours
  4. customwas produced as object compound

Sources & evidence

ORD record
ord-24e78789a79f4fc9af786e06b4056f44
Source dataset
uspto-grants-2005_02
Patent number
US06858721B2

Linked notes

Loading…