4-Toluenesulfonyl chloride → (6R)-8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 467259

Reaction equation

HRID 467259 reaction equation
C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.C(NC1SC=C(C(=NOC)C(O)=O)N=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(OC[C:56]1[CH2:65][S:64][C@@H:59]2[C@H:60](N)[C:61](=[O:62])[N:58]2[C:57]=1[C:66]([OH:68])=[O:67])=O>CC(N(C)C)=O.C(Cl)Cl>[S:64]1[C@@H:59]2[CH2:60][C:61](=[O:62])[N:58]2[C:57]([C:66]([OH:68])=[O:67])=[CH:56][CH2:65]1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 4413287-Aminocephalosporanic acidHCID 2724510(Z)-2-(2-Tritylaminothiazol-4-yl)-2-methoxyiminoacetic acid

Product 1

HCID 52921562(6R)-8-Oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-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-tritylamino-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-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Sources & evidence

ORD record
ord-c8c472ccf985436393c06c8da2cb919c
Source dataset
uspto-grants-1992_10
Patent number
US05159070

Linked notes

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