Triethylamine → [[3(S)-hydroxy-2-methylene-1-oxo-3-phenylpropyl]amino]acetic Acid Ethyl Ester

HRID 1007584Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1007584
C(N(CC)CC)C.Cl.[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH2:14])[CH3:10].[OH:16][C@@H:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18](=[CH2:22])[C:19](O)=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH2:9]([O:11][C:12](=[O:15])[CH2:13][NH:14][C:19](=[O:20])[C:18](=[CH2:22])[C@@H:17]([OH:16])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH3:10]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 235200933(S)-hydroxy-2-methylene-3-phenylpropanoic Acid

Produkt 1

HCID 69590134[[3(S)-hydroxy-2-methylene-1-oxo-3-phenylpropyl]amino]acetic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (3.75 mL, 0.027 mol, 1.2 eq) was added to a suspension of glycine ethyl ester hydrochloride (3.44 g, 0.024 mol, 1.1 eq) in anhydrous dichloromethane (60 mL) (see FIG. 4). The mixture was stirred for 15 min at room temperature and then cooled to 0° C. (ice bath). Compound 9a (4 g, 0.022 mol, 1 eq) and dicyclohexylcarbodiimide (5.09 g, 0.02469 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 with a 1N aqueous solution of HCl (50 mL), brine (50 mL) and dried over sodium sulfate. Evaporation of the solvent afforded an oil which was purified by column chromatography (eluent: hexane/EtOAc=6:4). The desired product 10a was obtained as a yellow oil (3.51 g, 60%). Rf0.25 (hexane/EtOAc=4:6). 1H NMR δ (CDCl3) 1.25 (t, 3H), 3.63 (s, 1H), 4.02 (m, 2H), 4.17 (q, 2H), 5.49 (s, 1H), 5.58 (d, 1H), 5.96 (s, 1H), 6.86 (s, 1H), 7.65 (m, 5H).[M+H]+ 264.1,: tR=2.55 min; purity: 96%.

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 with a 1N aqueous solution of HCl (50 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent
  7. customafforded an oil which
  8. customwas purified by column chromatography (eluent: hexane/EtOAc=6:4)

Quellen und Nachweise

ORD-Eintrag
ord-c5d8137e733140ecbbd0c92d115c7c65
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06794510B2

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