Ethanol → 5-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid

HRID 1845162Notes

Reaction equation

HRID 1845162 reaction equation
[CH2:1]([N:5]([CH3:26])[C:6]([C:8]1[CH:9]=[C:10]([C:21]([O:23]CC)=[O:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:13]=1)=[O:7])[CH:2]([CH3:4])[CH3:3].[OH-].[Li+].C(O)C>O>[CH2:1]([N:5]([CH3:26])[C:6]([C:8]1[CH:9]=[C:10]([C:21]([OH:23])=[O:22])[CH:11]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH:13]=1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 58188205Ethyl 5-(isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 581880895-(Isobutyl(methyl)carbamoyl)-4'-methylbiphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5-(isobutyl(methyl)carbamoyl)-4′-methylbiphenyl-3-carboxylate (165 mg, 0.467 mmol), lithium hydroxide (55 mg, 2.3 mmol), ethanol (10 mL), and water (1 mL) was stirred at room temperature for 5 h. LC-MS indicated completion of the reaction. The solvent was removed in vacuo and the residue was treated with water and acidified with 1N aq. HCl to pH=3 and extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to yield the product as white foam. LC-MS: 326.0 [M+1]+.

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed in vacuo
  3. additionthe residue was treated with water
  4. extractionextracted with EtOAc (50 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea93895823524f779d96ee687c0b961d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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