Triethylamine → N-[1-Oxo-2-(phenylmethyl)-2-propenyl]glycine Ethyl Ester

HRID 9783

Reaction equation

HRID 9783 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].[CH2:16]=[C:17]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18](O)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH:14][C:18](=[O:19])[C:17](=[CH2:16])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:10]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 3035712-Benzylacrylic AcidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 85937828N-[1-Oxo-2-(phenylmethyl)-2-propenyl]glycine Ethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3.10 mL, 0.022 mol, 1.2 eq) was added to a suspension of glycine ethyl ester hydrochloride (2.84 g, 0.020 mol, 1.1 eq) in anhydrous dichloromethane (100 mL) (see FIG. 6). The mixture was stirred for 15 min at room temperature and then cooled to 0° C. (ice bath). Compound 17 (3 g, 0.018 mol, 1 eq) and dicyclohexylcarbodiimide (4.19 g, 0.020 mol, 1.1 eq) were added successively to the reaction mixture which was stirred at room temperature for 17 h. The precipitate (dicyclohexylurea and triethylamine hydrochloride) was collected by filtration. The filtrate was washed successively with a saturated aqueous solution of sodium bicarbonate (100 mL), 1N aqueous solution of HCl (100 mL), brine (100 mL) and was then dried over sodium sulfate. Evaporation of the solvent afforded an oil which was purified by column chromatography (eluent:hexane/EtOAc=8:2). The desired product 18 was obtained as a solid (3.79 g, 83%). Rf=0.14 (hexane/EtOAc=7:3). m.p. 51° C. 1H NMR δ (CDCl3) 1.25 (t, 3H), 3.65 (s, 2H), 4.05 (d, 2H), 4.20 (q, 2H), 5.30 (s, 1H), 5.85 (s, 1H), 6.30 (s, 1H), 7.15–7.35 (m, 5H). [M+H]+ 248.0, tR=3.03 min; purity: 99.5%.

Workup

  1. temperaturecooled to 0° C. (ice bath)
  2. stirringwas stirred at room temperature for 17 h
  3. filtrationThe precipitate (dicyclohexylurea and triethylamine hydrochloride) was collected by filtration
  4. washThe filtrate was washed successively with a saturated aqueous solution of sodium bicarbonate (100 mL), 1N aqueous solution of HCl (100 mL), brine (100 mL)
  5. dry with materialwas then dried over sodium sulfate
  6. customEvaporation of the solvent
  7. customafforded an oil which
  8. customwas purified by column chromatography (eluent:hexane/EtOAc=8:2)

Sources & evidence

ORD record
ord-dc1ed22dc80b45699a119d3e840b40f3
Source dataset
uspto-grants-2006_08
Patent number
US07091354B2

Linked notes

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