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Hydrochloric Acid → (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoic acid

HRID 1816560
Notes
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Reaction equation

HRID 1816560 reaction equation
[CH:1]([O:4]/[C:5](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[O:21])[CH:13]=1)/[C:6]([O:8]CC)=[O:7])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[CH:1]([O:4]/[C:5](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)=[O:21])[CH:13]=1)/[C:6]([OH:8])=[O:7])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86759678ethyl (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoate

Product 1

HCID 22493906(Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

77 mg of ethyl (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoate was dissolved in 2 ml methanol, and 1 ml of 1N sodium hydroxide was added, and the mixture was stirred at room temperature for 22 hours. The reaction mixture was ice-cooled and neutralized with 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 44 mg of (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoic acid.

Workup

  1. temperaturecooled
  2. extractionby extracting with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-391b76bb5b5a40759134024a82d5b11e
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06884821B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes