Water → Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 330201
FC(F)(F)C(O)=O.[C:8]([C:11]([CH3:40])([CH3:39])[CH:12]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])O)([OH:10])=[O:9].C([SiH](CC)CC)C.O>C(Cl)(Cl)(Cl)Cl>[C:8]([C:11]([CH3:39])([CH3:40])[CH2:12][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][CH3:25])[CH:18]=[C:17]2[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][C:28]=1[O:37][CH3:38])([OH:10])=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 19870544Methyl 4-[5-(2-carboxy-1-hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Produkt 1

HCID 19870564Methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoateAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (1.25 g) was added slowly to a stirred solution of methyl 4-[5-(2-carboxy-1 hydroxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate 0.5 g) and triethylsilane (0.128 g) in carbon tetrachloride (7 ml) under an atmosphere of nitrogen. After 35 min, the mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were washed (water (4 times), brine), dried (MgSO4) and evaporated to give a dark oil. The product was purified by flash chromatography, eluting with 90:10:2 toluene:ethyl acetate:acetic acid, to give methyl 4-[5-(2-carboxy-2-methylpropyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate as an oil (0.27 g, 56%): partial NMR (250 MHz, DMSO-d6): 0.82(t, 3H, CH2CH3), 1.02(s, 6H, C(CH3)2), 1.68(m, 2H, CH2CH3), 291(s, 2H, C(CH3)2CH2), 3.82(s, 3H, OCH3), 3.89(s, 3H, OCH3), 4.01(m, 4H, NCH2, ArCH2Ar'), 12.15(br s, about 1H, COOH).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed (water (4 times), brine)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give a dark oil
  6. customThe product was purified by flash chromatography
  7. washeluting with 90:10:2 toluene

Quellen und Nachweise

ORD-Eintrag
ord-92804e4c38764e1886b9b2f5de314b36
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04894386

Notizen zur Reaktion

Wird geladen…