Diketene → 4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate
Reaction equation
Cl.[NH2:2][CH:3]1[C:24](=[O:25])[N:5]2[C:6]([C:11]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C[Si](CC(N)=O)(C)C.[CH2:46]=[C:47]1[O:51][C:49](=O)[CH2:48]1.BrBr.[N:54]([O-:56])=O.[Na+].[NH2:58][C:59]([NH2:61])=[S:60]>O1CCCC1.C(Cl)Cl.O>[NH2:61][C:59]1[S:60][CH:46]=[C:47]([C:48](=[N:54][OH:56])[C:49]([NH:2][CH:3]2[C:24](=[O:25])[N:5]3[C:6]([C:11]([O:13][CH2:14][C:15]4[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[CH:19][CH:20]=4)=[O:12])=[C:7]([Cl:10])[CH2:8][S:9][C@H:4]23)=[O:51])[N:58]=1Participants
11
Reactant 7
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (15.0 g.), bis(trimethylsilyl)acetamide (11.3 g.) and trimethylsilylacetamide (9.7 g.) in tetrahydrofuran (300 ml.), a solution of diketene (3.41 ml.) in methylene chloride (4 ml.), a solution of bromine (2.27 ml.) in methylene chloride (4 ml.), a solution of sodium nitrite (3.1 g.) in water (20 ml.) and a solution of thiourea (4.0 g.) in water (40 ml.) were treated in a similar manner to that of Example 37-(1) to give 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 10.4 g.).
Sources & evidence
- ORD record
- ord-259bfc055e864081b5390dd6a3de6cb4
- Source dataset
- uspto-grants-1989_06
- Patent number
- US04841062
Reaction notes
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