Ammonia → 2-Benzothiazolesulfonamide

HRID 466593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466593
C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1OCCO[C:28]1[CH:40]=[CH:39][C:31]2[N:32]=[C:33]([S:35]([NH2:38])(=[O:37])=[O:36])[S:34][C:30]=2[CH:29]=1)(=O)C.N>C(OCC)C>[S:34]1[C:30]2[CH:29]=[CH:28][CH:40]=[CH:39][C:31]=2[N:32]=[C:33]1[S:35]([NH2:38])(=[O:37])=[O:36]

Komponenten

4

Edukt 2

HCID 222AmmoniaHCID 867455416-[2'-(2",3",4",6"-tetra-O-acetyl-beta-glucopyranosyl)oxyethoxy]-2-benzothiazolesulfonamide

Produkt 1

HCID 679442-Benzothiazolesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

The unpurified 6-[2'-(2",3",4",6"-tetra-O-acetyl-β-glucopyranosyl)oxyethoxy]-2-benzothiazolesulfonamide (3.02 g.; 5.00 mmole) was dissolved in anhydrous diethyl ether (100 mL) and combined with cold (0° C.) saturated methanolic ammonia (100 mL) and stirred overnight with the temperature rising to room temperature over a six hour period. The solution was evaporated to dryness at reduced pressure and chromatographed on a silica gel column (150 g.) and eluted with chloroform/methanol (9.1). The product fractions (UV light and charring positive) were combined and evaporated to dryness at reduced pressure, and lyophilized to yield 6-[β-glucopyranosyl)oxyethoxy]-2-benzothiazolesulfonamide. The product conformed to accepted standards of purity and its structural assignment verified by standard spectroscopic methods (mass spec, 13C and 1H nuclear magnetic resonance).

Aufarbeitung

  1. waitrising to room temperature over a six hour period
  2. customThe solution was evaporated to dryness at reduced pressure
  3. customchromatographed on a silica gel column (150 g.)
  4. washeluted with chloroform/methanol (9.1)
  5. customevaporated to dryness at reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f0911f2161c546ae92983a6ae9af40e9
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157044

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