Phosphorus oxychloride → HCID 178502775, compound

HRID 1758069Notes

Reaction equation

HRID 1758069 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]3[NH:15][N:14]=[N:13][CH:12]=3)[CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.[S:29]1[CH:34]=[C:33]([C:35](=[N:39][O:40][CH3:41])[C:36](O)=[O:37])[S:32][CH2:31][CH2:30]1.P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.CN(C)C=O>[S:29]1[CH:34]=[C:33]([C:35](=[N:39][O:40][CH3:41])[C:36]([NH:1][CH:2]2[C:19](=[O:20])[N:4]3[C:5]([C:16]([OH:18])=[O:17])=[C:6]([CH2:9][S:10][C:11]4[NH:15][N:14]=[N:13][CH:12]=4)[CH2:7][S:8][C@H:3]23)=[O:37])[S:32][CH2:31][CH2:30]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 178508102HCID 178508102, compound

Product 1

HCID 178502775HCID 178502775, compoundYield 71.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-amino-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.57 g.) and trimethylsilylacetamide (4.6 g.) in ethyl acetate (20 ml.) and a mixture of 2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetic acid (syn isomer, 1.1 g.), N,N-dimethylformamide (0.44 g.) and phosphoryl chloride (0.92 g.) were treated in a similar manner to that of Example 21 to give 7-[2-(2,3-dihydro-1,4-dithiin-5-yl)-2-methoxyiminoacetamido]-3-(1H-1,2,3-triazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).

Workup

  1. additionwere treated in a similar manner to that of Example 21

Sources & evidence

ORD record
ord-f123299aac324f7382003677de274e70
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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