Methanesulfonyl chloride → HCID 15332425, compound

HRID 2100261Notes

Reaction equation

HRID 2100261 reaction equation
[CH2:1]([O:8][C@:9]1([CH:33]=[CH2:34])[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@@H:10]1[OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>N1C=CC=CC=1>[CH2:1]([O:8][C@:9]1([CH:33]=[CH2:34])[C@@H:13]([CH2:14][O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:12][C@@H:11]([N:23]2[CH:31]=[C:29]([CH3:30])[C:27](=[O:28])[NH:26][C:24]2=[O:25])[C@@H:10]1[O:32][S:36]([CH3:35])(=[O:38])=[O:37])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54435225HCID 54435225, compound

Product 1

HCID 15332425HCID 15332425, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

Nucleoside 24 (2.57 g, 5.53 mmol) was dissolved in anhydrous pyridine (18 cm3) and cooled to 0° C. Methanesulfonyl chloride (1.28 cm3, 16.6 mmol) was added dropwise and the mixture was stirred at room temperature for 30 min. The reaction was quenched with water (5 cm3) and the resulting mixture was extracted with dichloromethane (3×80 cm3). The combined extract was washed with saturated aqueous sodium hydrogencarbonate (3×120 cm3) and dried (Na2SO4). The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (99:1, v/v) as eluent to give nucleoside 25 as a yellow foam (2.53 g, 84%). δH (CDCl3) 8.92 (1H, br s, NH), 7.71 (1H, d, J 1.4, 6-H), 7.41-7.28 (10H, m, Bn), 6.57 (1H, d, J 7.8, 1′-H), 5.99-5.61 (4H, m, 2′-H, 1″-H and 2″-Ha, 2″-Hb), 4.86-4.50 (4H, m, Bn), 4.37 (1H, dd, J 1.5, 2.4, 4′-H), 8.82 (1H, dd, J 2.6, 11.0, 5′-Ha), 3.55 (1H, dd, J 1.2, 11.0, 5′-Hb), 3.02 (3H, s, CH3), 1.47 (3H, d, J 1.1, CH3). δC (CDCl3) 163.7 (C-4), 151.5 (C-2), 138.7, 136.7 (Bn), 135.7 (C-6), 130.9 (C-1″), 128.8, 128.5, 128.4, 127.6, 127.0 (Bn), 121.8 (C-2″), 111.9 (C-5), 85.1 (C-1′), 84.5 (C-3′), 84.0 (C-4′), 80.7 (C-2′), 73.7 (C-5′), 69.2, 67.7 (Bn), 38.9 (CH3), 11.8 (CH3).

Workup

  1. customThe reaction was quenched with water (5 cm3)
  2. extractionthe resulting mixture was extracted with dichloromethane (3×80 cm3)
  3. extractionThe combined extract
  4. washwas washed with saturated aqueous sodium hydrogencarbonate (3×120 cm3)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-758212029cac4fb9a9a9e85da2d5fbbf
Source dataset
uspto-grants-2009_08
Patent number
US07572582B2

Reaction notes

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