HCID 15334396, compound → HCID 21672598, compound

HRID 1007590Notes

Reaction equation

HRID 1007590 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 (1 H, d, J 1.2, 6-H), 7.50-7.23 (10 H, m, Bn), 6.22 (1 H, 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 (1 H, m,1″-Ha), 2.52 (1 H, 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. C27H30N2Ob,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-d8f5ab4645da44af86e3023f6a095d8f
Source dataset
uspto-grants-2004_09
Patent number
US06794499B2

Reaction notes

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