N4-Acetyl-2',3'-didehydro-2',3'-dideoxycytidine → N4-Acetyl-2',3'-dideoxycytidine

HRID 2209762Notes

Reaction equation

HRID 2209762 reaction equation
[C:1]([NH:4][C:5]1[CH:17]=[CH:16][N:8]([C@@H:9]2[O:15][C@H:12]([CH2:13][OH:14])[CH:11]=[CH:10]2)[C:7](=[O:18])[N:6]=1)(=[O:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([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:3])[CH3:2]

Participants

5

Reactant 2

HCID 14331712N4-Acetyl-2',3'-didehydro-2',3'-dideoxycytidineHCID 178418361HCID 178418361, compound

Product 1

HCID 14331714N4-Acetyl-2',3'-dideoxycytidineYield 77.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 33 (0.78 g, 3.1 mmol) in ethanol (100 mL) was hydrogenated under 15 psi of hydrogen gas in the presence of 10% Pd/C (0.15 g) for 12 hours. The reaction mixture was filtered, concentrated, and the residue was purified by chromatography over silica using 5% methanol in CHCl3 as the eluent to obtain 0.61 g (77.5%) of 34 as a colorless solid: mp 143°-145° C. (benzene-methanol); 1H NMR (DMSO-d6) δ 1.60-2.50 (7H, m, 2',3'-H and COCH3), 3.40-3.85 (2H, m, 5'-H), 3.90-4.30 (1H, m, 4'-H), 5.07 (1H, t, J=5.0 Hz, OH), 5.91 (1H, m, 1'-H), 7.17 (1H, d, J=7.6 Hz, 5-H), 8.32 (1H, d, J=7.3 Hz, 6-H), 10.80 (1H, s, NH).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customthe residue was purified by chromatography over silica using 5% methanol in CHCl3 as the eluent

Sources & evidence

ORD record
ord-e6b0511e3a1e4992b5daad23b84fc7cd
Source dataset
uspto-grants-1995_10
Patent number
US05455339

Reaction notes

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