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

HRID 516208Notes

Reaction equation

HRID 516208 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(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)+.

Workup

  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

Sources & evidence

ORD record
ord-519dce1acfab4bfeb53d8e82211be3f5
Source dataset
uspto-grants-2015_08
Patent number
US09108981B2

Reaction notes

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