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

HRID 1851794Notes

Reaction equation

HRID 1851794 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 thereto under ice-cooling, followed by stirring of the mixture overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogen sulfate 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
  2. temperatureunder ice-cooling
  3. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  4. additionwas 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-8ee39624e5334539a1136d2b9ae2e7a0
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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