Ammonia → Dideoxycytidine

HRID 2209763Notes

Reaction equation

HRID 2209763 reaction equation
C([NH:4][C:5]1[CH:17]=[CH:16][N:8]([C@@H:9]2[O:15][C@H:12]([CH2:13][OH:14])[CH2:11][CH2:10]2)[C:7](=[O:18])[N:6]=1)(=O)C.N>CO>[C@@H:9]1([N:8]2[CH:16]=[CH:17][C:5]([NH2:4])=[N:6][C:7]2=[O:18])[O:15][C@H:12]([CH2:13][OH:14])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 14331714N4-Acetyl-2',3'-dideoxycytidine

Product 1

HCID 24066DideoxycytidineYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 34 (0 6 g, 2.4 mmol ) in methanol saturated with ammonia (20 ml ) was stirred at 50° C. for 12 hours in a pressure vessel. The reaction mixture was concentrated and the residue was triturated with isopropanol, filtered, and dried to yield 0.4 g (80%) of 4: mp 207°-209° C. (benzene-ethanol); 1H NMR (DMSO-d6) δ 1.50-2.50 (4H, m, 2' and 3'-H), 3.63 (2H, m, 5'-H), 4.00 (1H, m, 4'-H), 4.96 (1H, t, J=4.9 Hz, OH), 5.69 (1H, d, J=7.25 Hz, 5-H), 5.95 (1H, m, 1'-H), 7.05 (2H, s, NH2), 7.89 (1 H, d, J=7.3 Hz, 6-H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was triturated with isopropanol
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-1f8aef3b23fd42d8acdba234106a25bb
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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