Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

HRID 1758077Notes

Reaction equation

HRID 1758077 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](CC(N)=O)(C)C.[S:34]1[CH:39]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41](O)=[O:42])[S:37][CH2:36][CH2:35]1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.CN(C)C=O>[S:34]1[CH:39]=[C:38]([C:40](=[N:44][O:45][CH3:46])[C:41]([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:42])[S:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 539358522-Methoxyimino-2-(2,3-dihydro-1,4-dithiin-5-yl)acetic acidHCID 703621504-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 1317120214-Nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylateYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (4.06 g.) and trimethylsilylacetamide (9.19 g.) in ethyl acetate (40 ml.) and a solution of 2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 2.2 g.), N,N-dimethylformamide (0.8 g.) and phosphoryl chloride (1.67 g.) in ethyl acetate (24 ml.) were treated in a similar manner to that of Example 19-(1) to give 4-nitrobenzyl 7-[2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.1 g.).

Sources & evidence

ORD record
ord-c5bd4dcad1d54be8a91683e6e988c010
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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