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

HRID 516208노트

반응식

HRID 516208 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

(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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-519dce1acfab4bfeb53d8e82211be3f5
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108981B2

반응 노트

불러오는 중…