Lithium hydroxide, monohydrate → 1-(3-Chlorobenzyl)-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid

HRID 623739Notes

Reaction equation

HRID 623739 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[C:7]1[C:22]([O:24]CC)=[O:23].O[Li].O>CCO.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][CH:29]=1)[CH2:5][N:6]1[C:10]([C:11]([F:13])([F:12])[F:14])=[CH:9][C:8]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[C:7]1[C:22]([OH:24])=[O:23]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86711828Ethyl 1-(3-chlorobenzyl)-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 867118291-(3-Chlorobenzyl)-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To crude ethyl 1-(3-chlorobenzyl)-3-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-2-carboxylate (732 mg, max. 1.57 mmol) in EtOH (2 mL) and H2O (2 mL) was added LiOH.H2O (347 mg, 8.28 mmol). The reaction mixture was stirred at reflux temperature overnight. The reaction mixture was concentrated, diluted with H2O (5 mL) and acidified with aqueous 1 M KHSO4 (10 mL) while cooling with an ice-bath. The precipitate was filtrated, washed with H2O (2×) and dried on filter to give ACI-07 (533 mg, 82% over two steps).

Workup

  1. temperatureat reflux temperature overnight
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with H2O (5 mL)
  4. temperaturewhile cooling with an ice-bath
  5. filtrationThe precipitate was filtrated
  6. washwashed with H2O (2×)
  7. customdried
  8. filtrationon filter
  9. customto give ACI-07 (533 mg, 82% over two steps)

Sources & evidence

ORD record
ord-b00fb694cfb44c338f198b11ef0a0164
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

Loading…