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

HRID 9780

反応式

HRID 9780 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%). Rf 0.25 (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%.

後処理

  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)

出典と根拠

ORDレコード
ord-b2591f3d8c244c90ae1d4040f2513ff7
出典データセット
uspto-grants-2006_08
特許番号
US07091354B2

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