Glutamic acid diethyl ester hydrochloride → diethyl(S)-2-(4-nitrophthalimido)glutarate

HRID 381582

反応式

HRID 381582 の反応式
C(N(C(C)C)CC)(C)C.[N+:10]([C:13]1[CH:14]=[C:15]2[C:20](=[O:21])[O:19][C:17](=O)[C:16]2=[CH:22][CH:23]=1)([O-:12])=[O:11].Cl.[CH2:25]([O:27][C:28](=[O:38])[C@H:29]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[NH2:30])[CH3:26]>C1(C)C=CC=CC=1.C(OCC)C>[N+:10]([C:13]1[CH:14]=[C:15]2[C:20](=[O:21])[N:30]([C@@H:29]([CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:27][CH2:25][CH3:26])=[O:38])[C:17](=[O:19])[C:16]2=[CH:22][CH:23]=1)([O-:12])=[O:11]

参加物

6

反応物 3

HCID 73960Glutamic acid diethyl ester hydrochlorideHCID 81531DiisopropylethylamineHCID 2309764-Nitrophthalic acid anhydride

生成物 1

HCID 10429715diethyl(S)-2-(4-nitrophthalimido)glutarate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

Diisopropylethylamine (24 ml, 0.138 mole) (Aldrich) was added to a suspension of 4-nitrophthalic anhydride (25 g, 0.13 mole) (Tokyo Kasei) and L-glutamic acid diethyl ester hydrochloride (35 g, 0.146 mole) (Aldrich) in toluene (130 ml). The reaction mixture was stirred at reflux utilizing a Dean-Stark trap for 2.5 hours. After cooling, the solution was diluted with diethyl ether (300 ml), washed with water (75 ml), saturated NaHCO3 solution (50 ml), dried (MgSO4), and concentrated in vacuo at 70° C. to give diethyl(S)-2-(4-nitrophthalimido)glutarate as an oil that solidified to a white solid on standing (35.8 g). M.P.=65.5-66.5° C. 1H NMR (DMSO-d6, 300 MHz) δ: 1.12 (t, J=7 Hz, 3H, ester CH3), 1.14 (t, J=7 Hz, 3H, ester CH3), 2.2-2.5 (m, 4H, glu CH2CH2), 3.96 (q, J=7 Hz, 2H, ester CH2), 4.08-4.19 (m, 2H, ester CH2), 4.97-5.04 (m, 1H, glu CH), 8.19 (dd, J=8,0.5 Hz, 1H, Ar), 8.56 (dd,=2,0.5 Hz, 1H, Ar), 8.68 (dd, J=8,2 Hz, 1H, Ar). Mass spectrum (CI—CH4); 379 (M+1, 28.8%), 333 (71.6%), 305 (100%). Anal. Calculated for C17H18N2O8: C, 53.97; H, 4.80; N, 7.40. Found: C, 53.89; H, 4.82; N, 7.42.

後処理

  1. temperatureat reflux
  2. customfor 2.5 hours
  3. temperatureAfter cooling
  4. washwashed with water (75 ml), saturated NaHCO3 solution (50 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo at 70° C.

出典と根拠

ORDレコード
ord-c511e394a895437eac28589c1e4caa66
出典データセット
uspto-grants-2001_10
特許番号
US06306865B1

関連ノート

読み込み中…