Triethylamine → HCID 86753804, compound

HRID 1417609Notes

Reaction equation

HRID 1417609 reaction equation
[Si]([O:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C@H:28]([OH:31])[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1)(C(C)(C)C)(C)C.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>ClCCl.C1COCC1.O>[OH:8][C:9]1[C:10]2[CH2:22][C@:21]3([CH3:35])[C@@H:23]([CH3:34])[CH2:24][CH2:25][C@H:26]4[C:27]([CH3:33])([CH3:32])[C@H:28]([O:31][S:44]([CH3:43])(=[O:46])=[O:45])[CH2:29][CH2:30][C@@:20]34[O:19][C:11]=2[C:12]2[CH2:13][NH:14][C:15](=[O:18])[C:16]=2[CH:17]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11078149TBAF tetrahydrofuranHCID 86753802HCID 86753802, compound

Product 1

HCID 86753804HCID 86753804, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the above Compound (36) (42 mg, 0.084 mmol) in 5 ml of dry dichloromethane were added 34 μl (0.244 mmol) of triethylamine and 14 μl (0.181 mmol) of methanesulfonyl chloride under ice-cooling, and the mixture stirred for 15 min at the same temperature. After addition of water, the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give an oil. This oil was dissolved in 2 ml of dry THF. To the solution was added 0.11 ml (0.11 mmol) of 1M tetrabutylammonium fluoride/THF solution under ice-cooling, and the mixture stirred for 20 min at the same temperature. After addition of ice-water, the reaction mixture was extracted with ethyl acetate. The extract was washed with 1N HCl, water, an aqueous saturated sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=15:1) to give 38 mg (98%) of Compound (13b).

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give an oil
  7. temperaturecooling
  8. stirringthe mixture stirred for 20 min at the same temperature
  9. extractionthe reaction mixture was extracted with ethyl acetate
  10. washThe extract was washed with 1N HCl, water
  11. dry with materialan aqueous saturated sodium hydrogen carbonate solution, and saturated brine, dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by a preparative thin layer chromatography (Merck, Kieselgel 60 F254, 0.5 mm; chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-3f13375c3dc34a0bbb1d7b6618555652
Source dataset
uspto-grants-1999_03
Patent number
US05876984

Reaction notes

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