Triethylamine → (S)-(3-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)isoxazol-5-yl)methyl methanesulfonate

HRID 710036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 710036
CCOC(C)=O.[F:7][C:8]([F:34])([C:23]1([OH:33])[CH2:28][C:27]([CH3:30])([CH3:29])[CH2:26][C:25]([CH3:32])([CH3:31])[CH2:24]1)[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[CH:20]=[C:19]([CH2:21][OH:22])[O:18][N:17]=1)=[O:10].CCN(CC)CC.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>O>[CH3:42][S:43]([O:22][CH2:21][C:19]1[O:18][N:17]=[C:16]([C@@H:12]2[CH2:13][CH2:14][CH2:15][N:11]2[C:9](=[O:10])[C:8]([F:7])([F:34])[C:23]2([OH:33])[CH2:24][C:25]([CH3:32])([CH3:31])[CH2:26][C:27]([CH3:30])([CH3:29])[CH2:28]2)[CH:20]=1)(=[O:45])=[O:44]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chloride2×HCID 86706747(S)-2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)-1-(2-(5-(hydroxymethyl)isoxazol-3-yl)pyrrolidin-1-yl)ethanone

Produkt 1

HCID 86706749(S)-(3-(1-(2,2-Difluoro-2-(1-hydroxy-3,3,5,5-tetramethylcyclohexyl)acetyl)pyrrolidin-2-yl)isoxazol-5-yl)methyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To an AcOEt (3 mL) solution of the compound (45 mg) obtained in Example 3-(4) and Et3N (31 μL), MsCl (13 μL) was added at 0° C. and after stirring the mixture for 30 minutes, MsCl (13 μL) was added and the mixture was stirred at 0° C. for 30 minutes, followed by addition of Et3N (31 μL) and stirring at 0° C. for 2.5 hours. The reaction mixture was added to water (50 mL) and the organic layer extracted with AcOEt (50 mL) was dried (MgSO4), filtered and concentrated to give the titled compound (58 mg, colorless oil.)

Aufarbeitung

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. stirringstirring at 0° C. for 2.5 hours
  3. extractionthe organic layer extracted with AcOEt (50 mL)
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3eb44b70f7854e7081166ab2b5d42f8f
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09181229B2

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