Sodium Hydroxide → 3-cyclohexyl-1-methyl-2-(2-{2-[methyl(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)amino]-2-oxoethoxy}phenyl)-1H-indole-6-carboxylic acid

HRID 1807635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807635
[OH-].[Na+].[CH:3]1([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([O:20]C)=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:22])[C:10]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][C:31]([N:33]([CH3:45])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][N:39]([CH3:44])[S:40](=[O:43])(=[O:42])[NH2:41])=[O:32])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>O.CO.C1COCC1>[CH:3]1([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH:16]=3)[N:11]([CH3:22])[C:10]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH2:30][C:31]([N:33]([CH3:45])[CH2:34][CH2:35][O:36][CH2:37][CH2:38][N:39]([CH3:44])[S:40](=[O:42])(=[O:43])[NH2:41])=[O:32])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 58317822methyl 3-cyclohexyl-1-methyl-2-(2-{2-[methyl(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)amino]-2-oxoethoxy}phenyl)-1H-indole-6-carboxylate

Produkt 1

HCID 583178273-cyclohexyl-1-methyl-2-(2-{2-[methyl(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)amino]-2-oxoethoxy}phenyl)-1H-indole-6-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of NaOH (1.00 g, 25 mmol) in water (5 mL) was added to a stirred solution of intermediate 7 (370 mg, 0.602 mmol) in MeOH (30 mL) and THF (10 mL). After 5 h, the solution was concentrated under vacuum. The pH was then adjusted to 5 with acetic acid (AcOH). Then, the reaction mixture was extracted with AcOEt, the organic layer dried over anhydrous Na2SO4, filtered and the filtrate evaporated to yield 300 mg (83%) of 3-cyclohexyl-1-methyl-2-(2-{2-[methyl(2-{2-[methyl(sulfamoyl)amino]ethoxy}ethyl)amino]-2-oxoethoxy}phenyl)-1H-indole-6-carboxylic acid 8 as a white powder: m/z=601 (M+H)+.

Aufarbeitung

  1. concentrationthe solution was concentrated under vacuum
  2. extractionThen, the reaction mixture was extracted with AcOEt
  3. dry with materialthe organic layer dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f68c1a5c7ef94ab2a245e18908dec6eb
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357687B2

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