p-methoxybenzyl 5-methoxymethyl-6H-1,3-thiazine-4-carboxylate → 3-Methoxymethyl-7beta-azido-7alpha-methoxy-3-cephem-4-carboxylate
Reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH2:9][S:8][CH:7]=[N:6][C:5]=1[C:10]([O:12]CC1C=CC(OC)=CC=1)=[O:11].CC1CSC=NC=1C(OCC(Cl)(Cl)Cl)=O.[C:37]([O:42][CH2:43][C:44]1[CH2:49][S:48][CH:47]=[N:46][C:45]=1[C:50]([O:52]COC)=[O:51])(=[O:41])[CH:38]([CH3:40])[CH3:39].[N:56]([CH:59]([O:63][CH3:64])[C:60](Cl)=[O:61])=[N+:57]=[N-:58]>>[CH3:1][O:2][CH2:3][C:4]1[CH2:9][S:8][C@@H:7]2[C@@:59]([N:56]=[N+:57]=[N-:58])([O:63][CH3:64])[C:60](=[O:61])[N:6]2[C:5]=1[C:10]([O-:12])=[O:11].[C:37]([O:42][CH2:43][C:44]1[CH2:49][S:48][C@@H:47]2[C@@:59]([N:56]=[N+:57]=[N-:58])([O:63][CH3:64])[C:60](=[O:61])[N:46]2[C:45]=1[C:50]([O-:52])=[O:51])(=[O:41])[CH:38]([CH3:39])[CH3:40]Participants
6
Reactant 4
Product 2
Procedure
Following the procedures described in Example 40 p-methoxybenzyl 5-methoxymethyl-6H-1,3-thiazine-4-carboxylate, 2,2,2-trichloroethyl 5-methyl-6H-1,3-thiazine-4-carboxylate or methoxymethyl 5-isobutyryloxymethyl-6H-1,3-thiazine-4-carboxylate are reacted with 2-azido-2-methoxyacetyl chloride to obtain p-methoxybenzyl dl-3-methoxymethyl-7β-azido-7α-methoxy-3-cephem-4-carboxylate, 2,2,2-trichloroethyl d1-3-methyl-7β-azido-7α-methoxy-3-cephem-4-carboxylate and methoxymethyl dl-3-isobutyryloxymethyl-7β-azido-7α-methoxy-3-cephem-4-carboxylate, respectively.
Sources & evidence
- ORD record
- ord-1161f07cb61348bf98c76edc3f0fd7f7
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962224
Reaction notes
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