Benzaldehyde → Diphenylmethyl 7-benzylideneamino-3-chloromethyl-3-cephem-4-carboxylate
Reaction equation
S(=O)(=O)(O)O.NC1C(=O)N2C(C([O-])=O)=C(C[N+]3(C)CCCC3)CS[C@H]12.Cl.[NH2:27][CH:28]1[C:53](=[O:54])[N:30]2[C:31]([C:37]([O:39][CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])=[C:32]([CH2:35][Cl:36])[CH2:33][S:34][C@H:29]12.[CH:55](=O)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1>>[CH:55](=[N:27][CH:28]1[C:53](=[O:54])[N:30]2[C:31]([C:37]([O:39][CH:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[O:38])=[C:32]([CH2:35][Cl:36])[CH2:33][S:34][C@H:29]12)[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1Participants
Reactant 4
Product 1
Procedure
Temperature stable crystalline mono-hydrochloric and sulfuric acid addition salts of 7-amino-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate substantially free of Δ2 isomer are intermediates for the preparation of broad spectrum 7-[α-(2-aminothiazol-4-yl)-α-(Z)-methoxyiminoacetamido]-3-[(1-methyl-1-pyrrolidinio)methyl]-3-cephem-4-carboxylates. The monohydrochloric acid addition salt intermediate is prepared by a process comprising the steps of (1) neutralizing diphenylmethyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride, (2) reacting the resulting free base with benzaldehyde to produce diphenylmethyl 7-benzylideneamino-3-chloromethyl-3-cephem-4-carboxylate, (3) reacting the resulting product with sodium iodide to convert the chloromethyl group to iodomethyl, (4) reacting the resulting product with N-methylpyrrolidine to give the quaternized product diphenylmethyl 7-benzylideneamino-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate iodide, and (5) reacting with hydrochloric acid to form said intermediate.
Workup
- customis prepared by a process
Sources & evidence
- ORD record
- ord-1755263a4b324b9c9a8299a10fc3b37d
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659812
Reaction notes
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