Ethyl Acetate → (S)-Phenyl(1-(3-chloro-2,6-difluorophenyl)-3-oxopropyl)carbamate

HRID 516208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 516208
[Cl:1][C:2]1[C:3]([F:17])=[C:4]([C:13]([F:16])=[CH:14][CH:15]=1)/[CH:5]=[N:6]/[S@](C(C)(C)C)=O.Cl[C:19]1[C:20](F)=[C:21]([C:24](F)=[CH:25][CH:26]=1)C=O.[C:29]([O-:32])([O-])=[O:30].[Cs+].[Cs+].CC([S@@](N)=O)(C)C.[CH3:42][CH2:43][O:44]C(C)=O>C(Cl)Cl>[C:19]1([O:32][C:29](=[O:30])[NH:6][C@H:5]([C:4]2[C:13]([F:16])=[CH:14][CH:15]=[C:2]([Cl:1])[C:3]=2[F:17])[CH2:42][CH:43]=[O:44])[CH:20]=[CH:21][CH:24]=[CH:25][CH:26]=1

Komponenten

7

Edukt 5

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 89405973(NE,S)-N-[(3-chloro-2,6-difluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

Produkt 1

HCID 89408383(S)-Phenyl(1-(3-chloro-2,6-difluorophenyl)-3-oxopropyl)carbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(S,E)-N-(3-Chloro-2,6-difluorobenzylidene)-2-methylpropane-2-sulfinamide: To a stirred suspension of 3-chloro-2,6-difluorobenzaldehyde (0.615g, 3.48 mmol) and Cs2CO3 (1.702 g, 5.23 mmol) in DCM (20 mL) was added a solution of (S)-2-methylpropane-2-sulfinamide (0.422 g, 3.48 mmol) in DCM (20 mL) dropwise for 10 min. The solution was then stirred at rt overnight. After overnight stirring, the reaction mixture was diluted with EtOAc and washed with brine (3×20 mL). The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product (0.98 g, 100%) as yellow oil. MS (ESI) m/z: 282.0 (M+H)+.

Aufarbeitung

  1. stirringAfter overnight stirring
  2. washwashed with brine (3×20 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-519dce1acfab4bfeb53d8e82211be3f5
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108981B2

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