Phosphorus oxychloride → HCID 131712014, compound

HRID 1758070Notes

Reaction equation

HRID 1758070 reaction equation
[O:1]1[C:6]([C:7](=[N:11][O:12][CH3:13])[C:8]([OH:10])=O)=[CH:5][S:4][CH2:3][CH2:2]1.P(Cl)(Cl)(Cl)=O.[NH2:19][CH:20]1[C:31](=[O:32])[N:22]2[C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]([CH3:27])[S:26][C@H:21]12.C[Si](CC(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[O:1]1[C:6]([C:7](=[N:11][O:12][CH3:13])[C:8]([NH:19][CH:20]2[C:31](=[O:32])[N:22]3[C:23]([C:28]([OH:30])=[O:29])=[CH:24][CH:25]([CH3:27])[S:26][C@H:21]23)=[O:10])=[CH:5][S:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 128022512-Methyl-7-amino-3-cephem-4-carboxylic acidHCID 53841578HCID 53841578, compound

Product 1

HCID 131712014HCID 131712014, compoundYield 57.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-methoxyiminoacetic acid (syn isomer, 1.4 g.), dry N,N-dimethylformamide (0.59 ml.) and phosphoryl chloride (1.17 g.) in dry ethyl acetate (12.3 ml.), and a solution of 7-amino-2-methyl-3-cephem-4-carboxylic acid (1.35 g.) and trimethylsilylacetamide (5.75 g.) in ethyl acetate (40 ml.) were treated in a similar manner to that of Example 14 to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-methoxyiminoacetamido]-2-methyl-3-cephem-4-carboxylic acid (syn isomer, 1.45 g.)

Sources & evidence

ORD record
ord-227d4111693c44fc85f722715cccc88b
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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