Hydrochloric Acid → FK-143

HRID 249167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249167
[NH2:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:8]=1)=[O:6].[CH2:25]([C:29]1[CH:34]=[CH:33][C:32]([CH:35](Cl)[C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH:43]([CH3:45])[CH3:44])=[CH:38][CH:37]=2)=[CH:31][CH:30]=1)[CH:26]([CH3:28])[CH3:27].C(N(C(C)C)CC)(C)C.Cl>ClCCl>[CH2:42]([C:39]1[CH:40]=[CH:41][C:36]([CH:35]([NH:1][C:2]2[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=2)[C:5]([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH:8]=2)=[O:6])[C:32]2[CH:33]=[CH:34][C:29]([CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:30][CH:31]=2)=[CH:37][CH:38]=1)[CH:43]([CH3:45])[CH3:44]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 11131084HCID 11131084, VerbindungHCID 19010817Bis(4-isobutylphenyl)chloromethane2×

Produkt 1

HCID 178077FK-143Ausbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 4-[3-(3-aminobenzoyl)indol-1-yl]butyric acid (880 mg), bis(4-isobutylphenyl)methyl chloride (1.03 g) and diisopropylethylamine (0.945 g) in dichloromethane (20 ml) was stirred at 25° C. overnight, and bis(4-isobutylphenyl)methyl chloride (170 mg) and diisopropylethylamine (86 mg) were added thereto. After stirring at 25° C. for 3 hours, the reaction mixture was poured into cold 1N hydrochloric acid. The organic layer was separated, washed with water, and dried over magnesium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (100 g) with a mixture of chloroform and methanol (50:1) as eluent and freeze-dried from benzene to give 4-[3-[3-(bis[4-isobutylphenyl)methylamino]benzoyl]indol-1-yl]butyric acid (820 mg) as pale yellow powder.

Aufarbeitung

  1. stirringAfter stirring at 25° C. for 3 hours
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (100 g) with a mixture of chloroform and methanol (50:1) as eluent
  7. dry with materialfreeze-dried from benzene

Quellen und Nachweise

ORD-Eintrag
ord-17efa2c6c99440988fb2363693c22d68
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212320

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