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1,2-Ethanediamine, N1,N2-bis(phenylmethyl)-, acetate (1:2) → 2-Methyl-2,3-methylene-6-[2-phenyl-2-(2-chlorophenoxy)acetamido]penam-3-carboxylic acid

HRID 1287330
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1287330
[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([O:9]CC(Cl)(Cl)Cl)=[O:8])[N:5]1[C:16](=[O:36])[CH:17]([NH:18][C:19](=[O:35])[CH:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C@H:4]1[S:3]2.C(O)(=O)C.C(O)(=O)C.[CH2:45]([NH:52][CH2:53][CH2:54][NH:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CN(C)C=O.C(O)(=O)C.CO.O.[Zn]>[CH2:45]([NH:52][CH2:53][CH2:54][NH:55][CH2:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1)[C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1.[CH3:1][C:2]12[CH2:15][C:6]1([C:7]([OH:9])=[O:8])[N:5]1[C:16](=[O:36])[CH:17]([NH:18][C:19](=[O:35])[CH:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:28])[C@H:4]1[S:3]2
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Komponenten

9

Edukt 2

HCID 312281,2-Ethanediamine, N1,N2-bis(phenylmethyl)-, acetate (1:2)HCID 681319712,2,2-Trichloroethyl 2-methyl-2,3-methylene-6-[2-phenyl-2-(2-chlorophenoxy)acetamido]penam-3-carboxylate

Produkt 2

HCID 8793BenzathineHCID 155824092-Methyl-2,3-methylene-6-[2-phenyl-2-(2-chlorophenoxy)acetamido]penam-3-carboxylic acidAusbeute 216 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23994ZincKatalysator
HCID 176Acetic AcidLösungsmittel
HCID 887MethanolLösungsmittel2×
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2,2,2-trichloroethyl 2-methyl-2,3-methylene-6-[2-phenyl-2-(2-chlorophenoxy)acetamido]penam-3-carboxylate (1.18 g.) in a mixture of dimethylformamide (5 ml.) and acetic acid (1.5 ml.) was added zinc powder (1.2 g.) under ice-cooling, and the mixture was stirred for 1.5 hours. After the reaction, the residue (0.65 g.) obtained by post-treating the reaction mixture in the similar manner as described in Example 1 was dissolved in methanol (2 ml.) and a solution of N,N'-dibenzylethylenediamine diacetate (0.20 g.) in water (10 ml.) was added to the solution. Crystals obtained in this manner were dissolved in methanol and subjected to reprecipitation with water to give N,N'-dibenzylethylenediamine salt of 2-methyl-2,3-methylene-6-[2-phenyl-2-(2-chlorophenoxy)acetamido]penam-3-carboxylic acid (0.55 g.), mp 107° to 110°C (dec.)

Aufarbeitung

  1. temperaturecooling
  2. customAfter the reaction
  3. customthe residue (0.65 g.) obtained
  4. additionby post-treating the reaction mixture in the similar manner
  5. customCrystals obtained in this manner
  6. customsubjected to reprecipitation with water

Quellen und Nachweise

ORD-Eintrag
ord-db632ec0447d41979d0fc0c130e957c1
Quelldatensatz
uspto-grants-1976_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03984397

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