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Ammonium Chloride → 7-[2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid

HRID 1154265
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1154265
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH2:27][C:28]([O:30]CC(Cl)(Cl)Cl)=[O:29])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.[Cl-].[NH4+]>O1CCCC1.O.[Zn]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:25][O:26][CH2:27][C:28]([OH:30])=[O:29])[C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[C:14]([C:20]([OH:22])=[O:21])=[C:15]([CH:18]=[CH2:19])[CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1
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Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 1317133477-[2-(2-Aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid

Produkt 1

HCID 913233527-[2-(2-Aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acidAusbeute 28,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysator
HCID 962
Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 7-[2-(2-aminothiazol-4-yl)-2-(2,2,2-trichloroethoxycarbonylmethoxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (0.5 g) in tetrahydrofuran (2.5 ml) were added zinc powder (0.5 g) and an aqueous ammonium chloride (0.3 g) in water (4 ml) at ambient temperature with stirring, and the stirring was continued at ambient temperature for 30 minutes. After the zinc powder was removed by filtration, the filtrate was adjusted to pH 2.3 with 10% hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride, followed by drying over magnesium sulfate. The solution was evaporated under reduced pressure, and the residue was triturated with diisopropyl ether to give 7-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid (syn isomer) (0.11 g).

Aufarbeitung

  1. customAfter the zinc powder was removed by filtration
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium chloride
  4. dry with materialby drying over magnesium sulfate
  5. customThe solution was evaporated under reduced pressure
  6. customthe residue was triturated with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-11c4f85e88c7470f91d0bf1aca15f66f
Quelldatensatz
uspto-grants-1984_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04487927

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