Hydrochloric Acid → 1-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-hydroxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamide

HRID 1909911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909911
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([NH:18][C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:39])[NH:28][S:29]([CH2:32][CH2:33][CH2:34][O:35]C(=O)C)(=[O:31])=[O:30])=[CH:23][CH:22]=3)[CH3:20])=[O:17])[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>O.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[C:16]([NH:18][C@H:19]([C:21]3[CH:26]=[CH:25][C:24]([C:27](=[O:39])[NH:28][S:29]([CH2:32][CH2:33][CH2:34][OH:35])(=[O:31])=[O:30])=[CH:23][CH:22]=3)[CH3:20])=[O:17])[CH:9]=[CH:8]2)=[CH:40][CH:41]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 583067451-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-acetoxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamide

Produkt 1

HCID 668684271-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-hydroxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of 1-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-acetoxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamide (200 mg), THF (3 mL), and methanol (3 mL) was added a 1 M aqueous sodium hydroxide solution (1.7 mL), followed by stirring at room temperature overnight. The reaction mixture was adjusted to pH 4 by adding 1 M hydrochloric acid (1.7 mL), and further, water (20 mL) was added thereto, followed by stirring at room temperature for 30 minutes. The precipitated solid was collected by filtration, washed with water (4 mL), and then washed with cold ethanol (3 mL) to obtain 1-(4-chlorobenzyl)-N-[(1S)-1-(4-{[(3-hydroxypropyl)sulfonyl]carbamoyl}phenyl)ethyl]-1H-indole-7-carboxamide (80 mg) as a pale yellow solid.

Aufarbeitung

  1. stirringby stirring at room temperature for 30 minutes
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water (4 mL)
  4. washwashed with cold ethanol (3 mL)

Quellen und Nachweise

ORD-Eintrag
ord-a1bf14455f0c48ee916a8aa4f56df42e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598355B2

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