Sodium Hydroxide → HCID 66670264, compound

HRID 1514638Notes

Reaction equation

HRID 1514638 reaction equation
[CH:1]1([C:7]2[N:11]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10]([CH3:21])=[C:9]([C:22]([O:24]CC)=[O:23])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:7]2[N:11]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10]([CH3:21])=[C:9]([C:22]([OH:24])=[O:23])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66670275HCID 66670275, compound

Product 1

HCID 66670264HCID 66670264, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 2.987 g portion of ethyl 5-cyclohexyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylate was dissolved in 16 ml of ethanol, and 13.37 ml of a 5 M sodium hydroxide aqueous solution was added thereto, followed by stirring at 80° C. for 40 hours. The reaction liquid was concentrated under a reduced pressure, and water was added to the residue. After washing with diethyl ether, 37% hydrochloric acid was added thereto until pH became 1. The resulting solid was collected by filtration and washed with water to obtain 1.859 g of 5-cyclohexyl-1-[2-(4-fluorophenyl)ethyl]-2-methyl-1H-pyrrole-3-carboxylic acid as a light brown solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under a reduced pressure, and water
  3. additionwas added to the residue
  4. washAfter washing with diethyl ether, 37% hydrochloric acid
  5. additionwas added
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-f26c0d5e324a4b8ea3e31da55f3d055f
Source dataset
uspto-grants-2012_07
Patent number
US08222274B2

Reaction notes

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