Ammonia → Deoxycytidine

HRID 2416123Notes

Reaction equation

HRID 2416123 reaction equation
C([NH:4][C:5]1[CH:18]=[CH:17][N:8]([C@@H:9]2[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]2)[C:7](=[O:19])[N:6]=1)(=O)C.N>>[C@@H:9]1([N:8]2[CH:17]=[CH:18][C:5]([NH2:4])=[N:6][C:7]2=[O:19])[O:16][C@H:13]([CH2:14][OH:15])[C@@H:11]([OH:12])[CH2:10]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11346228N4-Acetyl-2'-deoxycytidine

Product 1

HCID 13711DeoxycytidineYield 84.6%

Procedure

2′-deoxy-4-N-acetylcytidine is treated with methanolic ammonia overnight. The solution is concentrated in vacuo, and the residue is dissolved in water (100 mL) and is washed with dichloromethane (2×50 mL). The aqueous phase is evaporated in vacuo and the residue is purified on a column of Dowex 1-X2 (OH−)resin. The product is eluted with water, and the fractions are collected, evaporated and the residue is crystallized in methanol to give 2′-deoxycytidine (0.902 g, 84.6%). Melting point 208-210° C. 1H NMR (DMSO) d 1.94(dt, J=13.2, 6.1 Hz, 1, H2′), 2.12 (ddd, J=13.2, 6.0, 3.3 Hz, 1, H2″),3.07 (m, 2, H5′,5″), 3.77 (dd, J=6.9, 3.8 Hz, 1, H3′), 4.21 (dd, J=5.9, 3.2 Hz, 1, H4′), 5.02 (t, J=5.0 Hz, 1, OH5′), 5.23 (d, J=4.1 Hz, 1, OH3′), 5.75 (d, J=7.4 Hz, 1, H5), 6.17 (t, J=6.7 Hz, 1, H1′), 7.21 (br s, 2, NH2), 7.81 (d, J=7.4 Hz, 1, H6) ppm. MS (FAB) m/z 228.0990 (MH+[C9H14N3O4]=228.0984).

Workup

  1. concentrationThe solution is concentrated in vacuo
  2. dissolutionthe residue is dissolved in water (100 mL)
  3. washis washed with dichloromethane (2×50 mL)
  4. customThe aqueous phase is evaporated in vacuo
  5. customthe residue is purified on a column of Dowex 1-X2 (OH−)resin
  6. washThe product is eluted with water
  7. customthe fractions are collected
  8. customevaporated
  9. customthe residue is crystallized in methanol

Sources & evidence

ORD record
ord-1fa4ca2e5a48499a915842be4ea01af0
Source dataset
uspto-grants-2004_11
Patent number
US06822089B1

Reaction notes

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