(1,1'-Biphenyl)-4-carboxylic acid → 1-[(4-Biphenylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448722Notes

Reaction equation

HRID 448722 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[C:13]1([CH2:19][O:20][C:21]([C:23]2([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.ON1C2C=CC=CC=2N=N1.[C:40]1([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[CH:45]=[CH:44][C:43]([C:46](O)=[O:47])=[CH:42][CH:41]=1>C(Cl)Cl>[C:13]1([CH2:19][O:20][C:21]([C:23]2([NH:29][C:46]([C:43]3[CH:44]=[CH:45][C:40]([C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=4)=[CH:41][CH:42]=3)=[O:47])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[O:22])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 576728991-[(4-Biphenylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.11 g (11 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 2.33 g (10 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester, 1.68 g (11 mmol) of 1-hydroxybenzotriazole and 3.23 g (10 mmol) of 4-biphenylcarboxylic acid in 120 ml of methylene chloride under ice-cooling. After the mixture was stirred at room temperature overnight, the reaction solution was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography to obtain 3.51 g (85%) of the title compound.

Workup

  1. temperaturecooling
  2. concentrationthe reaction solution was concentrated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe mixture was successively washed with water
  5. dry with materialby drying with anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f69f0f37b4544b6a821f2e5a344cda00
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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