4-Toluenesulfonyl chloride → 3-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

HRID 467258Notes

Reaction equation

HRID 467258 reaction equation
C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[NH2:19][C:20]1[S:21][CH:22]=[C:23]([C:25](=[N:29][O:30][CH3:31])[C:26]([OH:28])=O)[N:24]=1.[CH3:32][C:33]([O:35][CH2:36][C:37]1[CH2:46][S:45][C@@H:40]2[C@H:41]([NH2:44])[C:42](=[O:43])[N:39]2[C:38]=1[C:47]([OH:49])=[O:48])=[O:34]>CC(N(C)C)=O.C(Cl)Cl>[C:33]([O:35][CH2:36][C:37]1[CH2:46][S:45][C@@H:40]2[CH:41]([NH:44][C:26](=[O:28])[C:25]([C:23]3[N:24]=[C:20]([NH2:19])[S:21][CH:22]=3)=[N:29][O:30][CH3:31])[C:42](=[O:43])[N:39]2[C:38]=1[C:47]([OH:49])=[O:48])(=[O:34])[CH3:32]

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 1317115033-Acetoxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

The process of claim 1 comprising reacting at low temperature, in dimethylacetamide, in the presence of triethylamine, tosyl chloride and the syn isomer of 2-(2-amino-4-thiazolyl)-2-methoxyimino-acetic acid and reacting the resulting product with 7-amino-cephalosporanic acid in methylene chloride in the presence of triethylamine to obtain the syn isomer of 3-acetoxymethyl-7[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Sources & evidence

ORD record
ord-de8da02fd2b34d2e9e843d0e7fc05bc2
Source dataset
uspto-grants-1992_10
Patent number
US05159070

Reaction notes

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