Sodium hydride → 4-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid ethyl ester

HRID 2292781Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2292781
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(Cl)Cl.CO.CCCCCC>O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:19][C:20]([NH2:22])=[O:21])=[C:7]([CH3:18])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)[CH3:33]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrateHCID 105657326-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamideHCID 21959077Hexane methylene chloride methanol

Produkt 1

HCID 105735094-(1-Benzyl-3-carbamoylmethyl-2-methyl-1H-indol-6-yloxy)-butyric acid ethyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 294 mg (1 mmol) of 6-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetamide was treated with 40 mg (1 mmol) of 60% NaH/mineral oil and after 1 hours, 0.15 mL (1 mmol) of ethyl 4-bromobutyrate was added. The mixture was stirred for 2 hours, diluted with water and extracted with EtOAc. The EtOAc solution was washed with NaCl solution, dried (MgSO4), and concentrated at reduced pressure. The residue was chromatographed on silica eluting with EtOAc to give (after crystallizing from CH2Cl2 /MeOH/hexane, 228 mg (76% yield) of 4-[[3-(2-amino-2-oxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-6-yl]oxy]butanoic acid ethyl ester, mp, 126°-133° C.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe EtOAc solution was washed with NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated at reduced pressure
  5. customThe residue was chromatographed on silica eluting with EtOAc
  6. customto give (

Quellen und Nachweise

ORD-Eintrag
ord-4c60fa18739745f09e8f5d5ad922be84
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05684034

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