Reaktion #602833

Reaktionsgleichung

hydroxylamine hydrochloride salt

phenolphthalein

compound 2

3-[4-[5-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentyl]-1,2,4-oxadiazol-3-yl]butyl]-5-methyl-1,3-benzoxazol-2-one

Sodium methoxide

→

solid

Ausbeute 52.0%

N′-hydroxy-5-(5-methyl-2-oxo-1,3-benzoxazol-3-yl)pentanamidine

Ausbeute 52.0%

Lösungsmittel

methanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux under an nitrogen atmosphere
2. 2
   Temperaturat reflux under a nitrogen atmosphere for 6 h
3. 3
   TemperaturThe reaction mixture was cooled
4. 4
   Einengenconcentrated in vacuo
5. 5
   Sonstigepurified by silica gel chromatography
6. 6
   Wascheneluting with 19:1 dichloromethane/methanol

Vorschrift

A solution of hydroxylamine hydrochloride salt (345 mg, 5.00 mmol) and phenolphthalein (1 crystal) in anhydrous methanol (5 ml) was stirred at reflux under an nitrogen atmosphere. Sodium methoxide was added portion-wise until a pink solution persisted (approximately 350 mg was used). The hot solution was filtered directly into a solution of compound 2 (115 mg, 0.50 mmol) in anhydrous ethanol (5 ml). The reaction mixture was stirred at reflux under a nitrogen atmosphere for 6 h. The reaction mixture was cooled, concentrated in vacuo and purified by silica gel chromatography eluting with 19:1 dichloromethane/methanol to give a brown solid (68 mg, 52%).

Quelle