Diethyl Ether → 3(RS)-amino-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide p-toluenesulphonate

HRID 635620Notes

Reaction equation

HRID 635620 reaction equation
C(OC([NH:8][CH:9]([CH2:23][C:24]([F:27])([F:26])[F:25])[C:10](=[O:22])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])=[O:12])=O)(C)(C)C.O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(OCC)C>C(#N)C>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[NH2:8][CH:9]([CH2:23][C:24]([F:25])([F:26])[F:27])[C:10](=[O:22])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=1[CH3:21])=[O:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 212590433(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide

Product 1

HCID 212588793(RS)-amino-5,5,5-trifluoro-2',4'-dimethyl-2-oxovaleranilide p-toluenesulphonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

194 mg (0.5 mmol) of 3(RS)-(tert-butoxyformamido)-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide and 285 mg (1.5 mmol) of p-toluenesulphonic acid monohydrate were dissolved in 5 ml of acetonitrile by heating to reflux for 15 seconds. The solution was allowed to cool and was stirred at room temperature for 1 hour. 20 ml of diethyl ether were added to the resulting suspension and the crude 3(RS)-amino-5,5,5-trifluoro-2′,4′-dimethyl-2-oxovaleranilide p-toluenesulphonate (1:1) which formed as a white solid was filtered off.

Workup

  1. temperatureby heating
  2. temperatureto reflux for 15 seconds
  3. temperatureto cool

Sources & evidence

ORD record
ord-c3c8c034c50f4cfa839bcd364d350816
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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