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

HRID 381582

반응식

HRID 381582 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-c511e394a895437eac28589c1e4caa66
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306865B1

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