Triethylamine → Ethyl oxo((2-oxo-2-phenylethyl)amino)acetate

HRID 1397340Notes

Reaction equation

HRID 1397340 reaction equation
C(N(CC)CC)C.Cl.[NH2:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].Cl[C:20](=[O:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(Cl)Cl.O>[O:26]=[C:20]([NH:9][CH2:10][C:11](=[O:12])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 2723597Ethanone, 2-amino-1-phenyl-, hydrochloride (1:1)

Product 1

HCID 12830685Ethyl oxo((2-oxo-2-phenylethyl)amino)acetateYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (36 mL, 262.1 mmol) was added to a solution of 2-aminoacetophenone hydrochloride (15.0 g, 87.39 mmol) in dry CH2Cl2 (300 mL), followed by ethyl chlorooxoacetate (10 mL, 87.39 mmol) at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 16 h. The mixture was then diluted with water and extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20-30% EtOAc in petroleum ether) to afford ethyl 2-oxo-2-((2-oxo-2-phenylethyl)amino)acetate (13.5 g, yield 66%). 1H NMR (400 MHz, CDCl3) δ 8.09 (br s, 1H), 8.02-8.00 (m, 2H), 7.68-7.64 (m, 1H), 7.55-7.51 (m, 2H), 4.85-4.84 (d, J=4.9 Hz, 2H), 4.44-4.39 (q, J=7.0 Hz, 2H), 1.44-1.41 (t, J=7.2 Hz, 3H). MS (ESI) m/z: Calculated for C12H13NO4: 235.08. found: 236.2 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with H2O and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography (silica gel 60-120 mesh, eluent 20-30% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-c1a1bd23966a41558a1d4de540a311c6
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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