Dicyclohexylcarbodiimide → benzoylmercaptoacetyl-N-hydroxysuccinimide

HRID 342334

Reaktionsgleichung

Reaktionsgleichung von HRID 342334
[C:1]([S:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][N:15]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]1=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[C:1]([S:9][CH2:10][C:11]([CH:17]1[CH2:18][C:19](=[O:20])[N:15]([OH:14])[C:16]1=[O:21])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 51165332-benzoylsulfanylacetic Acid

Produkt 1

HCID 86749986benzoylmercaptoacetyl-N-hydroxysuccinimideAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

To a stirring solution of (9.20 g, 46.9 mmoles) benzoylmercaptoacetic acid and (5.41 g, 46.9 mmoles) N-hydroxysuccinimide in (100 mL) dioxane was added a solution of (9.70 g, 47 mmoles) dicyclohexylcarbodiimide in (40 mL) dioxane. The reaction was stirred 12 hours followed by cooling to 4° C., filtering, and rotavapping off the dioxane to a white solid. The solid was triturated with cold isopropanol, filtered, and dried in vacuo yielding 10.8 g, 78% benzoylmercaptoacetyl-N-hydroxysuccinimide. 200 mg was recrystallized from 500 mg in hot ethyl acetate.

Aufarbeitung

  1. filtrationfiltering
  2. customThe solid was triturated with cold isopropanol
  3. filtrationfiltered
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-80b20cf679f04c699d08db924326939d
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05858327

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