1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → HCID 57304767, Verbindung

HRID 330204

Reaktionsgleichung

Reaktionsgleichung von HRID 330204
C([CH:4]([CH2:32][C:33](=[O:38])[NH:34][CH2:35][CH2:36][CH3:37])[CH:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=[C:10]2[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][C:21]=1[O:30][CH3:31])O)(O)=O.C(OC(OC(C)(C)C)N(C)C)(C)(C)C>C(Cl)Cl>[CH3:31][O:30][C:21]1[CH:22]=[C:23]([CH:28]=[CH:29][C:20]=1[CH2:19][C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([CH:5]=[CH:4][CH2:32][C:33](=[O:38])[NH:34][CH2:35][CH2:36][CH3:37])[CH:8]=2)[N:12]([CH2:16][CH2:17][CH3:18])[CH:11]=1)[C:24]([O:26][CH3:27])=[O:25]

Komponenten

4

Edukt 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 19870545Methyl 4-[5-(2-carboxy-1-hydroxy-3-(propylcarbamoyl)propyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Produkt 1

HCID 57304767HCID 57304767, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 4-[5-[2-carboxy-1-hydroxy-3-(propylcarbamoyl)propyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.81 g), and N,N-dimethylformamide di-tert-butyl acetal (1.54 ml, redistilled) in methylene chloride (26 ml) was stirred under a nitrogen atmosphere for 1 hour. The solvent was evaporated, and the product purified by flash chromatography, eluting with 4:1 ethyl acetate: hexane, to give methyl 3-methoxy-4-[1-propyl-5-[3-(propylcarbamoyl)prop-1-enyl]indol-3-ylmethyl]benzoate (0.56 g, 79%, as a separable mixture of olefin isomers) as a white solid: mp 140°-142°; E-olefin partial NMR (300 MHz, DMSO-d6): 0.83(m, 6H, 2×CH3), 3.82(s, 3H, OCH3), 3.92(s, 3H, OCH3). 6.15(d of t, 1H, olefinic-H), 6.47(d, J=15.9 Hz, 1H, olefinic-H), 7.86(t, 1H, NH), Z-olefin partial NMR (300 MHz, DMSO-d6 ): 0.82(m, 6H, 2×CH3), 3.82(s, 3H, OCH3), 3.90(s, 3H, OCH3), 5.70(m, 1H, olefinic-H), 6.57(d, J=11.5 HZ, 1H, olefinic-H), 7.86(t, 1H, NH).

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe product purified by flash chromatography
  3. washeluting with 4:1 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e115c0973ebd4f23836f8e23e8474a89
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894386

Verknüpfte Notizen

Wird geladen…