Lithium hydroxide, monohydrate → 1-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid

HRID 1665669

Reaction equation

HRID 1665669 reaction equation
O[Li].O.C[O:5][C:6]([C:8]1([C:11](=[O:25])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[CH2:10][CH2:9]1)=[O:7]>CO.C1COCC1.O>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][C:13]([NH:12][C:11]([C:8]2([C:6]([OH:7])=[O:5])[CH2:10][CH2:9]2)=[O:25])=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 578758101-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester

Product 1

HCID 578743681-(Biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acidYield 59.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (21 mg, 0.5 mmol) was added to a solution of 1-(biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid methyl ester (100 mg, 0.33 mmol) in methanol (0.5 mL), THF (1 mL) and H2O (0.3 mL) and the resulting mixture was stirred for 2 hours at ambient temperature. The reaction mixture was then concentrated and the residue was diluted with water, acidified with conc. HCl. The resulting precipitate was isolated by filtration and dried to afford 55 mg (58%) of 1-(biphenyl-4-ylcarbamoyl)-cyclopropanecarboxylic acid

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue was diluted with water
  3. customThe resulting precipitate was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-daf082de2add4ae18fb5243b49170445
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Linked notes

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