Methanol → 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid

HRID 2205422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2205422
C[O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH3:14])[CH:9]=[C:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:18][CH:17]=1)=[O:4].[OH-].[Na+].CO.O>C1COCC1>[C:23]([NH:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:8]2[C:7]3[C:11](=[CH:12][CH:13]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=3)[N:10]([CH3:14])[CH:9]=2)=[CH:21][CH:20]=1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 694530373-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester

Produkt 1

HCID 694497313-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 0.17 mmol), sodium hydroxide (21 mg, 0.52 mmol), methanol (3 mL), water (1 mL) and THF (3 mL) was heated to 60° C. for 24 hr. The reaction solution was then cooled to room temperature and concentrated in vacuo. The remaining residue was diluted with ethyl acetate (20 mL) and washed with 1N HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid (64 mg, 98% yield).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionThe remaining residue was diluted with ethyl acetate (20 mL)
  3. washwashed with 1N HCl (20 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-56a75832ce9a4ec4a1e012ad3350f535
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09371281B2

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