HCID 15334396, compound → HCID 21672598, compound

HRID 434258Notes

Reaction equation

HRID 434258 reaction equation
[CH2:1]([C@@:4]1([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:8]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:7][C@@H:6]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@@H:5]1[O:27]S(C)(=O)=O)[CH:2]=[CH2:3]>C(O)C.O.[OH-].[Na+]>[CH2:1]([C@@:4]1([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:8]([CH2:9][O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[O:7][C@@H:6]([N:18]2[CH:26]=[C:24]([CH3:25])[C:22](=[O:23])[NH:21][C:19]2=[O:20])[C@H:5]1[OH:27])[CH:2]=[CH2:3]

Participants

5

Reactant 1

HCID 15334396HCID 15334396, compound

Product 1

HCID 21672598HCID 21672598, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of nucleoside 3 (3.59 9, 6.45 mmol) in ethanol (72 cm3), water (72 cm3) and 1 M aqueous sodium hydroxide (20.6 cm3) was stirred under reflux for 18 h. After neutralisation with dilute hydrochloric acid, the solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (3×150 cm3). The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×200 cm3) and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1, v/v) as eluent to give 4 as a white solid material (2.32 g, 74%). δH (CDCl3) 7.60 (1H. d, J 1.2, 6-H), 7.50-7.23 (10 H, m, Bn), 6.22 (1H, d, J 2.9, 1′-H), 5.80 (1H, m, 2″-H), 5.15-5.08 (2 H, m, 3″-Ha, 3″-Hb), 4.86-4.33 (6 H, m, 2×Bn, 2′-H, 4′-H), 3.82-3.71 (2 H, m, 5′-Ha, 5′-Hb), 2.72 (1H, m, 1″-H), 2.52 (1H, dd, J 7.6, 16.1, 1″-Hb), 1.70 (3 H, d, J 0.9, CH3). δC (CDCl3) 165.1 (C-4), 150.4 (C-2), 138.4, 136.8 (Bn), 137.7 (C-6), 132.3 (C-2″), 128.77 128.4, 128.3, 128.0, 127.9, 127.6 (Bn), 118.5, (C-3″), 107.8 (C-5), 88.0, 87.8, 83.7 (C-1′, C-3′, C-4′), 73.7, 72.9, 69.4 (Bn, C-2′), 64.7 (C-5′), 31.1 (C-1″), 12.4 (CH3) (Found: C, 67.5; H, 6.3; N, 5.3. C27 H30N2O6,0.25 H2O requires C, 67.1; H, 6.4; N, 5.8%).

Workup

  1. temperatureunder reflux for 18 h
  2. customAfter neutralisation with dilute hydrochloric acid, the solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in dichloromethane (3×150 cm3)
  4. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×200 cm3)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-af1c9602bdab4b1ca474b31bd8ba67fa
Source dataset
uspto-grants-2003_12
Patent number
US06670461B1

Reaction notes

Loading…