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1-Aminocyclopropane-1-carboxylic acid → (E)-1-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)benzamido)cyclopropanecarboxylic acid

HRID 1503790
Notes
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Reaction equation

HRID 1503790 reaction equation
[F:1][C:2]([F:29])([F:28])[CH:3]([C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([Cl:26])=[C:21]([Cl:27])[CH:20]=1)/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1.S(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+].[NH2:40][C:41]1([C:44]([OH:46])=[O:45])[CH2:43][CH2:42]1>[Br-].C([N+](C)(C)C)CCCCCCCCCCC.ClC(Cl)C>[F:29][C:2]([F:28])([F:1])[CH:3]([C:19]1[CH:24]=[C:23]([Cl:25])[C:22]([Cl:26])=[C:21]([Cl:27])[CH:20]=1)/[CH:4]=[CH:5]/[C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:40][C:41]2([C:44]([OH:46])=[O:45])[CH2:43][CH2:42]2)=[O:12])=[C:8]([C:15]([F:17])([F:18])[F:16])[CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 5351-Aminocyclopropane-1-carboxylic acidHCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 867225822-(trifluoromethyl)-4-[(E)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl]benzoic acid

Product 1

HCID 86722602(E)-1-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)benzamido)cyclopropanecarboxylic acid
Yield 77.1%

Reagents, catalysts & solvents 2

HCID 14249Dodecyltrimethylammonium bromideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A 250 mL round bottomed (rb) flask equipped with a magnetic stir bar, temperature probe and reflux condenser was charged with (E)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)benzoic acid (5.3 g, 11.10 mmol) and dichloroethane (DCE) (40 mL). Thionyl chloride (1.620 mL, 22.19 mmol) was added neat in one portion and the resulting reaction mixture was heated at reflux for 2.5 h. After which time the reaction mixture was allowed to cool and then concentrated to give the crude acid chloride which was used without further purification. The acid chloride intermediate was taken up in anhydrous THF (56 mL) and was added to a 250 mL flask equipped with a magnetic stir bar, a temperature probe and a reflux condenser. While stirring, dodecyltrimethylammonium bromide (0.03 g, 0.111 mmol), sodium carbonate (0.932 g, 11.10 mmol) and 1-aminocyclopropanecarboxylic acid (1.6 g, 12.0 mmol) were added in this order and stirred at reflux overnight. The reaction was allowed to cool and the white solid residue was filtered via vacuum filtration. The filtrate was concentrated to afford the title compound as a light brown solid (4.8 g, 77%). This material was used without further purification.

Workup

  1. customA 250 mL round bottomed (rb) flask equipped with a magnetic stir bar
  2. temperaturetemperature probe and reflux condenser
  3. customthe resulting reaction mixture
  4. temperaturewas heated
  5. temperatureat reflux for 2.5 h
  6. temperatureto cool
  7. concentrationconcentrated
  8. customto give the crude acid chloride which
  9. customwas used without further purification
  10. additionwas added to a 250 mL flask
  11. customequipped with a magnetic stir bar
  12. stirringstirred
  13. temperatureat reflux overnight
  14. temperatureto cool
  15. filtrationthe white solid residue was filtered via vacuum filtration
  16. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9f4681dce6b54bdcb92a681352e6a326
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09212164B2

Reaction notes

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