Sodium Hydroxide → 1-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]-1H-indole-6-carboxylic acid

HRID 2208595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2208595
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9][CH:8]=1)=[O:6]>CO.C1COCC1>[C:22]([O:21][C:19]([NH:18][CH2:17][CH2:16][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:15]=2)[CH:11]=[CH:12]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86725264HCID 86725264, Verbindung

Produkt 1

HCID 247209431-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]-1H-indole-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydroxide (1N, 6.0 mL, 6.00 mmol) was added to a solution of 1-(2-tert-Butoxycarbonylamino-ethyl)-1H-indole-6-carboxylic acid methyl ester (0.501 g, 1.57 mmol) in methanol (12 mL) and THF (4.0 mL). The reaction was stirred at room temperature for 68 hr. The reaction was concentrated in vacuo. The aqueous residue was acidified to pH˜1 with 1N HCl and extracted with ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 327 (M+Na)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was carried forward without purification

Quellen und Nachweise

ORD-Eintrag
ord-1403971dc47245af97d3a0700af6ba93
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09376454B2

Notizen zur Reaktion

Wird geladen…