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

HRID 516208ノート

反応式

HRID 516208 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

(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)+.

後処理

  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

出典と根拠

ORDレコード
ord-519dce1acfab4bfeb53d8e82211be3f5
出典データセット
uspto-grants-2015_08
特許番号
US09108981B2

反応ノート

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