Phosphorus oxychloride → HCID 131712323, compound

HRID 745408Notes

Reaction equation

HRID 745408 reaction equation
[NH2:1][CH:2]1[C:12](=[O:13])[N:4]2[C:5]([C:9]([OH:11])=[O:10])=[CH:6][CH2:7][S:8][C@H:3]12.C[Si](CC(N)=O)(C)C.[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH3:40])[C:31](O)=[O:32])[N:29]=1)=[O:23].P(Cl)(Cl)(Cl)=O>C(OCC)(=O)C.CN(C)C=O>[CH:22]([NH:24][C:25]1[S:26][CH:27]=[C:28]([C:30](=[N:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH3:40])[C:31]([NH:1][CH:2]2[C:12](=[O:13])[N:4]3[C:5]([C:9]([OH:11])=[O:10])=[CH:6][CH2:7][S:8][C@H:3]23)=[O:32])[N:29]=1)=[O:23]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 357676Acetamide, 2-(trimethylsilyl)-HCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 54222530HCID 54222530, compound

Product 1

HCID 131712323HCID 131712323, compoundYield 83.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 7-amino-3-cephem-4-carboxylic acid (1.3 g.) and trimethylsilylacetamide (7.0 g.) in ethyl acetate (30 ml.) and a solution of 2-(2-formamidothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetic acid (syn isomer, 1.72 g.), N,N-dimethylformamide (0.48 g.) and phosphoryl chloride (1.01 g.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-ethoxyethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 2.35 g.).

Sources & evidence

ORD record
ord-bb1de8332180461d8ab7ec640aa55783
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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