Hydrochloric Acid → Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate

HRID 1904467Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904467
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]2[CH2:13][C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=1[O:24][CH3:25].[CH:26]1([CH2:31][C:32](O)=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1.Cl.CN(C)CCCN=C=NCC.Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:26]1([CH2:31][C:32]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]3[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 71606Cyclopentylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23365902HCID 23365902, Verbindung

Produkt 1

HCID 14626833Methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoateAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of the ester (H) described above (used without further characterization) (4.43 g), cyclopentylacetic acid (1.85 g), 4-(dimethylamino)pyridine (1.76 g), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.26 g), was dissolved in methylene chloride (100 ml), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml), the separated aqueous layer extracted with dichloromethane (2×100 ml), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethanol to give off-white needles which were recrystallized from methylene chloride/hexane to give methyl 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoate (I) as a white powder (5.12 g, 87%); mp 144°-146° C.; partial NMR (250 MHz, DMSO-d6): 1.17(m, 2H), 1.32(t, 3H), 1.4-1.8(m, 6H), 2.25(m, 3H), 3.82(s, 3H, OCH3), 3.92(s, 3H, OCH3), 3.97 (s, 2H, ArCH2), 4.09(q, 2H, CH2CH3), 9.61(s, 1H, NH).

Aufarbeitung

  1. extractionthe separated aqueous layer extracted with dichloromethane (2×100 ml)
  2. washthe combined organic extracts washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residual oil was crystallized from ethanol
  6. customto give off-white needles which
  7. customwere recrystallized from methylene chloride/hexane

Quellen und Nachweise

ORD-Eintrag
ord-6d15baa4e911421483a426202ee775ae
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04837235

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