Water → HCID 15334396, compound

HRID 1663515Notes

Reaction equation

HRID 1663515 reaction equation
[CH2:1]([C@@:4]1([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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[OH:27])[CH:2]=[CH2:3].[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>N1C=CC=CC=1>[CH2:1]([C@@:4]1([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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[O:27][S:37]([CH3:36])(=[O:39])=[O:38])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 21672597HCID 21672597, compound

Product 1

HCID 15334396HCID 15334396, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of nucleoside 2 (3.50 g, 7.31 mmol) in anhydrous pyridine (23 cm3) at 0° C. was added methanesulphonyl chloride (1.69 cm3, 21.89 mmol). The reaction mixture was stirred for 1 h at room temperature, water (100 cm3) was added and extraction was performed using 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 purified by silica gel column chromatography using dichloromethane/methanol (99:1) as eluent to give 3 as a white solid material (3.64 g, 89%). δH (CDCl3) 8.95 (1 H, br s, NH), 7.71 (1 H, d, J 1.1, 6-H), 7.39-7.25 (10 H, m, Bn), 6.52 (1 H, d, J 8.0, 1′-H), 5.90 (1H, m, 2″-H), 5.34 (1 H, d, J 7.9, 2′-H), 5.20-5.09 (2 H, m, 3″-Ha, 3″-Hb), 4.91 (1 H, d, J 11.2, Bn), 4.68 (1 H, d, J 11.3, Bn), 4.64 (2 H, s, Bn), 4.33 (1 H, br s, 4′-H), 3.81 (1 H, dd, J 2.5, 11.1, 5′-Ha), 3.73 (1 H, dd, J 1.1, 11.1, 5′-Hb), 3.08 (1 H, dd, J 5.5, 5.7, 1″-Ha), 2.99 (3 H, s, CH3), 2.68 (1 H, m, 1″-Hb), 1.51 (3 H, d, J 0.8, CH3). δC (CDCl3) 163.4 (C-4), 150.8 (C-2), 137.9, 136.3 (Bn), 135.5 (C-6), 131.0 (C-2″), 128.8, 128.3, 127.5, 127.2 (Bn), 119.3 (C-3″), 111.6 (C-5), 84.1, 83.6, 82.4, 82.2 (C-1′, C-2′, C-3′, C-4′), 73.7, 68.9 (Bn), 66.2 (C-5′), 38.7 (CH3), 33.0 (C-1″), 11.9 (CH3) (Found: C, 60.5; H, 5.8; N, 4.9. C28H32N2O8S requires C, 60.4; H, 5.8; N, 5.0%).

Workup

  1. extractionextraction
  2. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×200 cm3)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6ad488a626fe4490aeb24553b67d13ac
Source dataset
uspto-grants-2011_10
Patent number
US08034909B2

Reaction notes

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