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Trimethylacetamide → 7-[2-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 255757
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 255757
P(Cl)(Cl)(Cl)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][O:22][CH:23]=[O:24])[C:15]([OH:17])=O)[N:13]=1)=[O:7].[NH2:25][CH:26]1[C:43](=[O:44])[N:28]2[C:29]([C:40]([OH:42])=[O:41])=[C:30]([CH2:33][S:34][C:35]3[S:36][CH:37]=[N:38][N:39]=3)[CH2:31][S:32][C@H:27]12.CC(C)(C)C(N)=O>C(OCC)(=O)C.O.CN(C)C=O>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:18][O:19][CH2:20][CH2:21][O:22][CH:23]=[O:24])[C:15]([NH:25][CH:26]2[C:43](=[O:44])[N:28]3[C:29]([C:40]([OH:42])=[O:41])=[C:30]([CH2:33][S:34][C:35]4[S:36][CH:37]=[N:38][N:39]=4)[CH2:31][S:32][C@H:27]23)=[O:17])[N:13]=1)=[O:7]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 12957TrimethylacetamideHCID 24813Phosphorus oxychlorideHCID 128891877-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acidHCID 541333172-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetic acid

Produkt 1

HCID 1317152837-[2-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
Ausbeute 31,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

Dry N,N-dimethylformamide (1.2 g.), phosphoryl chloride (2.5 g.), 2-(2-formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetic acid (syn isomer, 3.8 g.) and dry ethyl acetate (49.7 ml.) were treated in a similar manner to that of Example 1-(1) to give an activated acid solution. The solution was added to a solution of 7-amino-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (4.4 g.) and trimethylacetamide (12.3 g.) in dry ethyl acetate (90 ml.) at -10° C., and stirred at -5° to -10° C. for an hour. Water (50 ml.) was added to the resultant solution and allowed to stand at room temperature. The ethyl acetate layer was separated, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After concentrating the solution in vacuo, the residue was pulverized with diisopropyl ether. The precipitates were collected by filtration, washed with diisopropyl ether and dried to give 7-[2-(2 -formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 2.5 g.).

Aufarbeitung

  1. customto give an activated acid solution
  2. customto stand at room temperature
  3. customThe ethyl acetate layer was separated
  4. washwashed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationAfter concentrating the solution in vacuo
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with diisopropyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1f983e88b55e43529e619a55e7c98532
Quelldatensatz
uspto-grants-1987_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04698337

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