Triethylamine → 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

HRID 839147

Reaktionsgleichung

Reaktionsgleichung von HRID 839147
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](NCC(O)=O)=[CH:5][CH:4]=1.[CH2:14]([O:18]C(Cl)=O)[CH:15](C)C.[CH3:22][C:23]1[S:24][C:25]([S:28][CH2:29][C:30]2[CH2:37][S:36][CH:35]3[N:32]([C:33](=[O:39])[CH:34]3[NH2:38])[C:31]=2[C:40]([OH:42])=[O:41])=[N:26][N:27]=1.C([N:45](CC)CC)C>>[CH3:22][C:23]1[S:24][C:25]([S:28][CH2:29][C:30]2[CH2:37][S:36][CH:35]3[N:32]([C:33](=[O:39])[CH:34]3[NH:38][C:14](=[O:18])[CH:15]([C:6]3[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=3)[NH2:45])[C:31]=2[C:40]([OH:42])=[O:41])=[N:26][N:27]=1

Komponenten

5

Edukt 4

HCID 8471Triethylamine2×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 203258583-[(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

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 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
  3. customthe amine protecting group is removed by acid hydrolysis

Quellen und Nachweise

ORD-Eintrag
ord-a2dfcdbd52ed4c59a7405d7b36dd8a9a
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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