1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-[2-(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetylsulfamoyl]-butyric acid methyl ester

HRID 1445912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1445912
[CH2:1]([N:8]1[C:16]2[C:11](=[C:12]([O:17][CH2:18][C:19](O)=[O:20])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][S:29](=[O:32])(=[O:31])[NH2:30].CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:23][O:24][C:25](=[O:33])[CH2:26][CH2:27][CH2:28][S:29](=[O:31])(=[O:32])[NH:30][C:19](=[O:20])[CH2:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:11]=1[CH:10]=[C:9]([CH3:22])[N:8]2[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10511613Methyl 4-sulfamoylbutanoateHCID 18461534(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid

Produkt 1

HCID 685477134-[2-(1-Benzyl-2-methyl-1H-indol-4-yloxy)-acetylsulfamoyl]-butyric acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid (5) (0.189 g, 0.64 mmole) in dichloromethane (15 mL), 4-sulfamoyl-butyric acid methyl ester (0.232 g, 1.28 mmole), EDCI (0.122 g, 0.64 mmole) and DMAP (0.078 g, 0.64 mmole) were added. The mixture was stirred at room temperature for 18 h. The dichloromethane was evaporated to half of the original volume and the mixture was washed with water (2×10 mL). The organic layer was separated and evaporated. The residue was purified by column chromatography (10:1 CHCl3:MeOH) to afford intermediate (6) as a solid. Yield: 0.15 g, 51%

Aufarbeitung

  1. customThe dichloromethane was evaporated to half of the original volume
  2. washthe mixture was washed with water (2×10 mL)
  3. customThe organic layer was separated
  4. customevaporated
  5. customThe residue was purified by column chromatography (10:1 CHCl3:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-695312058b34417980a41988dd6d0801
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

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