Phenylacetyl chloride → 1-[(Phenylacetyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448721Notes

Reaction equation

HRID 448721 reaction equation
C(N(CC)CC)C.[C:8]1([CH2:14][O:15][C:16]([C:18]2([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[C:8]1([CH2:14][O:15][C:16]([C:18]2([NH:24][C:32](=[O:33])[CH2:31][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)=[O:17])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 576728391-[(Phenylacetyl)amino]cyclohexanecarboxylic acid phenylmethyl esterYield 91.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.21 g (12 mmol) of triethylamine was added to a solution of 2.33 g (10 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester in 100 ml of tetrahydrofuran, and 1.55 g (10 mmol) of phenylacetyl chloride was added dropwise to the mixture under ice-cooling, followed by stirring of the mixture overnight. Under reduced pressure, the reaction solution was concentrated, 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 3.21 g (91%) of the title compound.

Workup

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

Sources & evidence

ORD record
ord-6ca1b4f3c89449ed864fdef5b2b9a54d
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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