Chloroacetaldehyde → Ethenodeoxycytidine

HRID 366970

Reaction equation

HRID 366970 reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.Cl[CH2:18][CH:19]=O>CS(C)=O>[CH2:2]1[C@H:1]([N:9]2[C:10](=[O:11])[N:12]3[C:13](=[N:14][CH:18]=[CH:19]3)[CH:15]=[CH:16]2)[O:8][C@H:5]([CH2:6][OH:7])[C@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 13711Deoxycytidine

Product 1

HCID 107769Ethenodeoxycytidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

3,N4 -Ethenodeoxycytidine is synthesized according to the published procedure of Eberle et al. (Carcinogenesis 10:2751-2756, 1989). To 2'-deoxycytidine (8 mg, available from Sigma Chemical Company) in 0.4 mL of DMSO is added 0.04 mL of a 45% aqueous solution of chloroacetaldehyde and the reaction mixture is stirred for 1 hour at 70° C. The reaction mixture is then evaporated to dryness and the resulting residue purified by reverse-phase HPLC on a Nucleosil C18 column (Altech) to yield 3,N4 -ethenodeoxycytidine.

Workup

  1. custom3,N4 -Ethenodeoxycytidine is synthesized
  2. customThe reaction mixture is then evaporated to dryness
  3. customthe resulting residue purified by reverse-phase HPLC on a Nucleosil C18 column (Altech)

Sources & evidence

ORD record
ord-39f7cef867664f9b9434a2a4f9b1958b
Source dataset
uspto-grants-2000_10
Patent number
US06132776

Linked notes

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