Octylamine → HCID 19375130, Verbindung

HRID 128800

Reaktionsgleichung

Reaktionsgleichung von HRID 128800
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl[S:11]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([NH:9][S:11]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([OH:20])=[O:19])=[CH:21][CH:22]=1)(=[O:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:1]([NH:9][S:11]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][OH:19])=[CH:21][CH:22]=1)(=[O:13])=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Komponenten

6

Edukt 3

HCID 8143OctylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 21226445Aluminium lithium hydride

Produkt 2

HCID 19375130HCID 19375130, VerbindungHCID 54342163HCID 54342163, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-(Octylaminosulfonyl)benzoic acid is prepared in the usual way from octylamine and 4-(chlorosulfonyl)benzoic acid. This material is reduced with lithium aluminum hydride in THF in the usual fashion, and purified by chromatography with 1:3 ethyl acetate-dichloromethane to provide 4-(octylaminosulfonyl)benzyl alcohol as a colorless solid in 54% yield. Swern oxidation (DMSO-oxalyl chloride, dichloromethane) of this material provides 4-(octylaminosulfonyl)benzaldehyde as a colorless solid after chromatography. By the method of example 1(A), but using two equivalents of the phosphonium ylide, the aldehyde is chain-extended and converted to the dimethyl acetal, and by the method of example 2 this is condensed with glyoxylic acid to provide the title compound as a colorless solid, mp 223°-224° after recrystallization from ethyl acetate.

Aufarbeitung

  1. custompurified by chromatography with 1:3 ethyl acetate-dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-a71d66e4014744c48529560a4d05b868
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464865

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