Water → 1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Water	HCID 962	—
Edukt	Acetic acid, 2-oxo-, methyl ester	HCID 70205	—
Edukt	3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one	HCID 21519177	—
Lösungsmittel	Benzene	HCID 241	—
Produkt	1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one	HCID 53714964	64%

Reaktionsschritte

3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio) azetidin-2-one (526mg) and methyl glyoxylate (1.17g) were refluxed in dry benzene (25ml) with provision for the removal of water. After 11/2 hours the solvent was evaporated and the residue was chromatographed on silica to give 1-(1-hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (399 mg). νmax (CHCl3) 3475 (--OH), 1770 (β-lactam), 1750 (ester) cm-1.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US03939157
Quelldatensatz	uspto-grants-1976_02
ORD ID	ord-3cc90c8cd3aa4749b64a735c745c1059
Quellennotiz	uspto-grants-1976_02