Ethanesulfonyl chloride → HCID 19348792, Verbindung

HRID 1418142Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418142
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][C:12]=1[NH:19][C:20](=[O:38])[CH2:21][CH:22]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl.C(OCC)(=O)C>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][NH:18][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:13][C:12]=1[NH:19][C:20](=[O:38])[CH2:21][CH:22]([C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH3:8])([CH3:9])[CH3:10]

Komponenten

5

Edukt 2

HCID 11667Ethanesulfonyl chlorideHCID 19348478HCID 19348478, Verbindung

Produkt 1

HCID 19348792HCID 19348792, VerbindungAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

180 μl (1.90 mmol) of ethanesulfonyl chloride and then 213 mg (1.75 mmol) of 4-N,N-dimethylaminopyridine were added to a solution of 700 mg (1.59 mmol) of N-[2-t-butyl-5-(aminomethyl)phenyl]-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Preparation 26A) in 15 ml of methylene chloride, whilst cooling in an ice-salt bath, and the resulting mixture was stirred at the same temperature for 1 hour. At the end of this time, the reaction mixture was diluted with ethyl acetate, and the diluted solution was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 38 g of silica gel, using a 3:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 360 mg of the title compound as a foam-like substance.

Aufarbeitung

  1. temperaturewhilst cooling in an ice-salt bath
  2. washthe diluted solution was washed with water, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. dry with materialafter which it was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through 38 g of silica gel
  6. additionby volume mixture of ethyl acetate and hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-d7fdb425c3de450a8cfa2ecdc1f01172
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05880147

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