Sodium Hydroxide → (1-Carbamoyl-1H-indol-3-yl)-acetic acid

HRID 1527198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527198
C([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:15](=[O:17])[NH2:16])[CH:7]=1)C.[OH-].[Na+]>CO.O>[C:15]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([CH2:5][C:4]([OH:18])=[O:3])=[CH:7]1)(=[O:17])[NH2:16]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68283759(1-carbamoyl-1H-indol-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 68283440(1-Carbamoyl-1H-indol-3-yl)-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of (1-carbamoyl-1H-indol-3-yl)-acetic acid ethyl ester in methanol (61 mL) and water (6.1 mL) was added an 1N aqueous solution of NaOH (12.2 mL, 12.2 mmol) and the resulting yellow solution was stirred at RT for 4 h. The reaction mixture was concentrated under reduced pressure and the residue was suspended in HCl 1N. The aqueous mixture was extracted with EtOAC (3×), the combined organic extracts were dried (phase separator) and concentrated in vacuo. The crude product was used directly in the next step without any further purification. MS: 219 [M+H]+, 437 [2M+H]+; tR (HPLC conditions b) 2.16 min.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe aqueous mixture was extracted with EtOAC (3×)
  3. customthe combined organic extracts were dried (phase separator)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was used directly in the next step without any further purification
  6. customtR (HPLC conditions b) 2.16 min.

Quellen und Nachweise

ORD-Eintrag
ord-f8ace63ab6fa41f5ba75bf6487303067
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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