Hexane → 3-(3-Ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid

HRID 431096

Reaktionsgleichung

Reaktionsgleichung von HRID 431096
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH2:16][CH3:17])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].[CH3:18][C:19]1[CH:20]=[C:21]2[C:26](=O)[O:25][C:23](=[O:24])[C:22]2=[CH:28][CH:29]=1.C(OCC)(=O)C.CCCCCC>C(O)(=O)C.O>[CH2:16]([O:15][C:9]1[CH:8]=[C:7]([CH:2]([N:1]2[C:26](=[O:25])[C:21]3=[CH:20][C:19]([CH3:18])=[CH:29][CH:28]=[C:22]3[C:23]2=[O:24])[CH2:3][C:4]([OH:6])=[O:5])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14])[CH3:17]

Komponenten

7

Edukt 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 880694-Methylphthalic anhydrideHCID 41021513-Amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid

Produkt 1

HCID 219886643-(3-Ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of 3-amino-3-(3-ethoxy-4-methoxyphenyl)propanoic acid (3.00 g, 12.5 mmol) and 4-methylphthalic anhydride (2.13 g, 12.5 mmol, 95%) in acetic acid was heated to reflux under nitrogen for 18 hours. The mixture was allowed to cool to room temperature. The solvent was removed in vacuo to give an oil. The resulting oil was stirred with ethyl acetate (10 mL), hexane (10 mL) and water (30 mL) for 30 minutes. The resulting suspension was filtered. The solid was washed with water (3×10 mL) and hexane (3×10 mL), and then was dried in a vacuum oven overnight (60° C., <1 torr) to give 3-(3-ethoxy-4-methoxyphenyl)-3-(4-methylphthalimido)propanoic acid as a white solid (3.4 g, 71% yield): mp, 134.0-136.0° C.; 1H NMR (DMSO-d6) δ1.31 (t, J=6.9 Hz, 3H, CH3), 2.47 (s, 3H, CH3), 3.23 (dd, J=6.7, 16.5 Hz, 1H, CHH), 3.50 (dd, J=9.2, 16.5 Hz, 1H, CHH), 3.72 (s, 3H, CH3), 3.97 (q, J=6.9 Hz, 2H, CH2), 5.58 (dd, J=6.7, 9.1 Hz, 1H, NCH), 6.90-6.95 (m, 2H, Ar), 7.01 (br s, 1H, Ar), 7.61-7.76 (m, 3H, Ar), 12.4 (br s, 1H, OH); 13C NMR (DMSO-d6) δ14.65, 21.32, 36.09, 50.04, 55.45, 63.72, 111.79, 112.15, 119.29, 123.08, 123.58, 128.51, 131.35, 131.49, 134.95, 145.63, 147.75, 148.53, 167.67, 167.78, 171.72; Anal Calcd for C21H21NO6: C, 65.79; H, 5.52; N, 3.65. Found: C, 65.46; H, 5.57; N, 3.31.

Aufarbeitung

  1. temperatureto reflux under nitrogen for 18 hours
  2. customThe solvent was removed in vacuo
  3. customto give an oil
  4. filtrationThe resulting suspension was filtered
  5. washThe solid was washed with water (3×10 mL) and hexane (3×10 mL)
  6. customwas dried in a vacuum oven overnight (60° C., <1 torr)

Quellen und Nachweise

ORD-Eintrag
ord-a82f1ce421da440fa5d09c05a27376e8
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06656964B2

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