4-Toluenesulfonyl chloride → 3-Acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid
Reaction equation
C(N(CC)CC)C.S(Cl)(C1C=CC(C)=CC=1)(=O)=O.[C:19]([NH:38][C:39]1[S:40][CH:41]=[C:42]([C:44](=[N:48][O:49][CH3:50])[C:45]([OH:47])=O)[N:43]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH3:51][C:52]([O:54][CH2:55][C:56]1[CH2:65][S:64][C@@H:59]2[C@H:60]([NH2:63])[C:61](=[O:62])[N:58]2[C:57]=1[C:66]([OH:68])=[O:67])=[O:53]>CC(N(C)C)=O.C(Cl)Cl>[C:52]([O:54][CH2:55][C:56]1[CH2:65][S:64][C@@H:59]2[CH:60]([NH:63][C:45](=[O:47])[C:44]([C:42]3[N:43]=[C:39]([NH:38][C:19]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[S:40][CH:41]=3)=[N:48][O:49][CH3:50])[C:61](=[O:62])[N:58]2[C:57]=1[C:66]([OH:68])=[O:67])(=[O:53])[CH3:51]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
Another preferred embodiment of the process of the invention comprises reacting at low temperatures in dimethylacetamide in the presence of triethylamine, tosyl chloride and the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetic acid and reacting the resulting product with a solution of 7-amino-cephalosporanic acid in methylene chloride in the presence of triethylamine to obtain the syn isomer of 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-methoxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.
Sources & evidence
- ORD record
- ord-3f3a1292495f4743810503f73b4d9110
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05159070
Reaction notes
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