HCID 15334396, compound → HCID 21672598, compound

HRID 659836Notes

Reaction equation

HRID 659836 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 g, 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 (10H, m, Bn), 6.22 (1H, d, J 2.9, 1′-H), 5.80 (1H, m, 2″-H), 5.15-5.08 (2H, m, 3″-Ha, 3″-Hb), 4.86-4.33 (6H, m, 2×Bn, 2′-H, 4′-H), 3.82-3.71 (2H, m, 5′-Ha, 5′-Hb), 2.72 (1H, m, 1″-Ha), 2.52 (1H, dd, J 7.6, 16.1, 1″-Hb), 1.70 (3H, 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. C27H30N2O6, 0.25H2O 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-3f7558a9d740465b9e682597fd6cbaf6
Source dataset
uspto-grants-2011_12
Patent number
US08080644B2

Reaction notes

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