Water → (R,E)-Ethyl 2-(N-(4-cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetate

HRID 1429409Notes

Reaction equation

HRID 1429409 reaction equation
[C:1](/[CH:3]=[CH:4]/[C@H:5]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:27])([F:26])[F:25])(=[O:16])=[O:15])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[C:1](/[CH:3]=[CH:4]/[C@H:5]([N:13]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][C:24]([F:25])([F:26])[F:27])(=[O:15])=[O:16])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 71269687(R,E)-N-(4-Cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)benzenesulfonamide

Product 1

HCID 71277869(R,E)-Ethyl 2-(N-(4-cyano-1-phenylbut-3-en-2-yl)-2-(trifluoromethoxy)phenylsulfonamido)acetateYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 31g (4.2 g, 10.6 mmol) in DMF (100 mL) was added ethyl bromoacetate (2.1 g, 12.7 mmol) and K2CO3 (3.5 g, 25.4 mmol). The mixture was stirred at rt for 12 h, then water (100 mL) was added to the mixture. The mixture was extracted with EA three times and the combined organic layer was washed with brine and dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by CC (hexane/EA=5:1) to give compound 31h (3.7 g, 73% yield).

Workup

  1. extractionThe mixture was extracted with EA three times
  2. washthe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated
  6. customthe residue was purified by CC (hexane/EA=5:1)

Sources & evidence

ORD record
ord-1f005715df5243969acff34ea0290f5b
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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