Trifluoroacetic acid → 4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid

HRID 494752Notes

Reaction equation

HRID 494752 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([CH2:12][C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[CH:4][C:3]=1[Cl:32].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5]([CH2:12][C:13]([C:22]([O:24][CH2:25][CH3:26])=[O:23])([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][C:15]([OH:17])=[O:16])=[CH:4][C:3]=1[Cl:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68590557Tert. butyl 4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butyrate2×

Product 1

HCID 221846134-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.0 g (62.25 mmol) tert. butyl 4-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-3,3-bis-ethoxycarbonyl-butyrate (Intermediate product 65) in 200 mL CH2Cl2 was added 20 mL TFA while cooling with ice and the mixture was stirred for 16 hours at RT. The reaction mixture was evaporated i. vac. and the residue recrystallised from petroleum ether. The precipitate was filtered off, washed with petroleum ether and dried.

Workup

  1. temperaturewhile cooling with ice
  2. customThe reaction mixture was evaporated i
  3. customand the residue recrystallised from petroleum ether
  4. filtrationThe precipitate was filtered off
  5. washwashed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-bea2455ae5c8407e9ce1bdd836c3241d
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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