4-Toluenesulfonyl chloride → 3-Methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-{2-bromoethoxyimino}-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 981548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981548
C([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][CH2:33][Br:34])[C:27]([OH:29])=O)[N:25]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[CH3:46][S:47][CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:59]([NH2:60])[C:58](=[O:61])[N:53]2[C:54]=1[C:55]([OH:57])=[O:56]>C(O)=O>[CH3:46][S:47][CH2:48][C:49]1[CH2:50][S:51][C@@H:52]2[CH:59]([NH:60][C:27](=[O:29])[C:26]([C:24]3[N:25]=[C:21]([NH2:20])[S:22][CH:23]=3)=[N:30][O:31][CH2:32][CH2:33][Br:34])[C:58](=[O:61])[N:53]2[C:54]=1[C:55]([OH:57])=[O:56]

Komponenten

5

Edukt 3

HCID 73974-Toluenesulfonyl chlorideHCID 537601652-(2-Tritylamino-4-thiazolyl)-2-(2-bromoethoxyimino)-acetic acidHCID 677128833-Methylthiomethyl-7-amino-ceph-3-eme-4-carboxylic acid

Produkt 1

HCID 1317167903-Methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-{2-bromoethoxyimino}-acetamido]-ceph-3-eme-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

Using the procedure of Example 17, 1.909 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-(2-bromoethoxyimino)-acetic acid (described in French Pat. No. 2,438,050), 0.68 g of tosyl chloride, 0.927 g of 3-methylthiomethyl-7-amino-ceph-3-eme-4-carboxylic acid and 15 ml of 67% aqueous formic acid were reacted to obtain 0.615 g of pure syn isomer of 3-methylthiomethyl-7-[2-(2-amino-4-thiazolyl)-2-{2-bromoethoxyimino}-acetamido]-ceph-3-eme-4-carboxylic acid with a melting point of 185° C. (decomposition).

Quellen und Nachweise

ORD-Eintrag
ord-aefddb9c06e74d279ba53c9572312f5b
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04992431

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