Triethylamine → 3-[(Acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester

HRID 839148Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839148
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6](NCC(O)=O)=[CH:5][CH:4]=1.ClC([O:17][CH2:18][CH:19](C)C)=O.[C:22]([O:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH2:46])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24].C([N:50](CC)CC)C>>[C:22]([O:28][CH2:29][O:30][C:31]([C:33]1[N:34]2[CH:37]([S:38][CH2:39][C:40]=1[CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH:36]([NH:46][C:18](=[O:17])[CH:19]([C:6]1[CH:5]=[CH:4][C:3]([CH2:2][Cl:1])=[CH:8][CH:7]=1)[NH2:50])[C:35]2=[O:47])=[O:32])(=[O:27])[C:23]([CH3:25])([CH3:26])[CH3:24]

Komponenten

5

Edukt 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 128109063-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl esterHCID 22767740p-Chloromethylphenylglycine

Produkt 1

HCID 541348743-[(Acetyloxy)methyl]-7-[[2-[4-(chloromethyl)phenyl]-2-aminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid pivalyloxymethyl ester

Versuchsvorschrift

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

Aufarbeitung

  1. customThe thus obtained
  2. customThe resulting product is isolated
  3. customthe amine protecting group is removed by acid hydrolysis
  4. additionby treating the product with difluoroacetic acid for 5 minutes at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-3abed74665a0414e92ca52182cfbe613
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093804

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