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Water → 1,1-Dimethylethyl 4-[1-(diphenylmethyl)-3-azetidinyl]hexahydro-1H-1,4-diazepine-1-carboxylate

HRID 1384795
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1384795
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10](OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23](=[O:26])([O-])[O-:24].[K+].[K+].O.ClCCl.CO.[C:35](#[N:37])[CH3:36]>>[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([N:37]3[CH2:11][CH2:10][CH2:9][N:8]([C:23]([O:24][C:1]([CH3:7])([CH3:6])[CH3:2])=[O:26])[CH2:36][CH2:35]3)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonateHCID 21226129Dichloromethane methanol

Produkt 1

HCID 211837621,1-Dimethylethyl 4-[1-(diphenylmethyl)-3-azetidinyl]hexahydro-1H-1,4-diazepine-1-carboxylate

Versuchsvorschrift

To a solution of 1-diphenylmethyl-3-methanesulphonyloxyazetidine (WO 96/05193) (25 g) in acetonitrile (800 mL) were added the compound of PREPARATION 24 (19 g) and potassium carbonate (33 g). The reaction mixture was heated to reflux for 12 h, then cooled to room temperature. Water was added to the resulting slurry, and the mixture extracted three times with ethyl acetate. The combined organics were washed with brine, dried over magnesium sulphate, filtered and dried in vacuo to yield crude product. Chromatography on silica gel eluting with dichloromethane:methanol (95:5) yielded the title compound (24.7 g).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 h
  3. extractionthe mixture extracted three times with ethyl acetate
  4. washThe combined organics were washed with brine
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customdried in vacuo
  8. customto yield crude product

Quellen und Nachweise

ORD-Eintrag
ord-56965c0a85c7480881ad8a711f4fef68
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06262046B1

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