Dicyclohexylcarbodiimide → N-(13-benzyloxycarbonyltridecanoyloxy)sulfosuccinimide sodium salt

HRID 1742086

Reaktionsgleichung

Reaktionsgleichung von HRID 1742086
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:27]1[C:31](=[O:32])[CH2:30][CH:29]([S:33]([OH:36])(=[O:35])=[O:34])[C:28]1=[O:37].[Na:38].C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C=O>[Na:38].[CH2:1]([O:8][C:9]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][N:27]1[C:31](=[O:32])[CH2:30][CH:29]([S:33]([OH:36])(=[O:35])=[O:34])[C:28]1=[O:37])=[O:23])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 1401212414-(Benzyloxy)-14-oxotetradecanoic acidHCID 86222747sodium N-hydroxysulfosuccinimide

Produkt 1

HCID 86748065N-(13-benzyloxycarbonyltridecanoyloxy)sulfosuccinimide sodium saltAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

In 0.4 ml of anhydrous dimethyl formamide was dissolved 1,14-tetradecanedioic acid monobenzyl ester (100 mg, 0.29 mmole). To the obtained solution were added sodium N-hydroxysulfosuccinimide (63 mg, 0.29 mmole) and a solution of DCC (65 mg, 0.29 mmole) in 0.4 ml of anhydrous dimethylformamide and the resulting mixture was stirred for 14 hours at a room temperature. The reaction mixture was filtered and the filtrate was stirred for 2 hours at a temperature under ice cooling. The solid that formed was collected by filtration and dried under reduced pressure to give N-(13-benzyloxycarbonyltridecanoyloxy)sulfosuccinimide sodium salt (66 mg, 42%) having the following properties.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered
  2. customThe solid that formed
  3. filtrationwas collected by filtration
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cf4e49fb98e940e3a76c0aa80dc46901
Quelldatensatz
uspto-grants-1994_08
Patentnummer
US05336782

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