Phosphorus oxychloride → 7-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid

HRID 1284776Notes

Reaction equation

HRID 1284776 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:10]([OH:12])=O)[N:8]=1)=[O:2].P(Cl)(Cl)(Cl)=O.[NH2:23][CH:24]1[C:34](=[O:35])[N:26]2[C:27]([C:31]([OH:33])=[O:32])=[CH:28][CH2:29][S:30][C@H:25]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C>C(OCC)(=O)C.CN(C)C=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:10]([NH:23][CH:24]2[C:34](=[O:35])[N:26]3[C:27]([C:31]([OH:33])=[O:32])=[CH:28][CH2:29][S:30][C@H:25]23)=[O:12])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 11708267BistrimethylsilylacetamidHCID 12941984(6R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 539721442-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid

Product 1

HCID 1317124827-[2-(2-Formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acidYield 32.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid (syn isomer, 3.47 g.), N,N-dimethylformamide (1.1 g.) and phosphoryl chloride (2.3 g.) in ethyl acetate (35 ml.), and a solution of 7-amino-3-cephem-4-carboxylic acid (2.5 g.) and bis(trimethylsilyl)acetamide (12.7 g.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 15-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2-chloroethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.85 g.).

Sources & evidence

ORD record
ord-86974c18fbe94f91b0661953c45e1ff8
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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