Triethylamine → 1-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

HRID 891682Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 891682
[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:15][CH:14]([OH:16])[CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3].[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:4][C:5]([C:7]1[N:8]=[C:9]([N:12]2[CH2:13][CH:14]([O:16][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:15]2)[S:10][CH:11]=1)=[O:6])[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22242912HCID 22242912, Verbindung

Produkt 1

HCID 222429401-(4-Allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (2.91 g, 11.1 mmol) (obtained as described in Reference Example 41(2)) in methylene chloride (146 ml) were added methanesulfonyl chloride (2.58 ml, 33.3 mmol) and triethylamine (4.67 ml, 33.3 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 2 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. To the residue were added ethyl acetate and diisopropyl ether, and then the mixture was filtered and the resulting residue was washed with diisopropyl ether to give 1-(4-allyloxycarbonyl-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (2.71 g, yield 77%) as pale brown crystals.

Aufarbeitung

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. additionTo the residue were added ethyl acetate and diisopropyl ether
  8. filtrationthe mixture was filtered
  9. washthe resulting residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3ba7254b2b8045d4ac0673638c9424ea
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07001897B2

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