Isobutyl chloroformate → 8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2398964

Reaktionsgleichung

Reaktionsgleichung von HRID 2398964
ClCC1C=CC(NCC(O)=O)=CC=1.C(OC(Cl)=O)C(C)C.CC1SC(SC[C:30]2[CH2:37][S:36][CH:35]3[N:32]([C:33](=[O:39])[CH:34]3N)[C:31]=2[C:40]([OH:42])=[O:41])=NN=1>C(N(CC)CC)C>[O:39]=[C:33]1[N:32]2[CH:35]([S:36][CH2:37][CH:30]=[C:31]2[C:40]([OH:42])=[O:41])[CH2:34]1

Komponenten

5

Edukt 3

HCID 62365Isobutyl chloroformateHCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 22767740p-Chloromethylphenylglycine

Produkt 1

HCID 190919938-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel2×

Versuchsvorschrift

p-Chloromethylphenylglycine wherein the amino group is protected with tert-butoxycarbonyl is treated with isobutylchloroformate in the presence of triethylamine. The thus obtained anhydride is reacted with the triethylamine salt of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid at 0° C. for about 4 hours.The resulting product is isolated, and the amine protecting group is removed by acid hydrolysis to give 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-[[2-[4-chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

Aufarbeitung

  1. customThe resulting product is isolated
  2. customthe amine protecting group is removed by acid hydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-414e91285bcc45d6883b4cd3486af122
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04026887

Verknüpfte Notizen

Wird geladen…