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

HRID 9783

Reaktionsgleichung

Reaktionsgleichung von HRID 9783
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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-dc1ed22dc80b45699a119d3e840b40f3
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091354B2

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