Pyridine → Phenylacetyl 7-aminodesacetoxycephalosporanic acid

HRID 1833895Notes

Reaction equation

HRID 1833895 reaction equation
[CH3:1][C:2]1([CH3:24])[CH:6]([C:7]([OH:9])=[O:8])[N:5]2[C:10](=[O:22])[C@@H:11]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C@H:4]2[S@:3]1=O.ClC(Cl)(Cl)COP([O-])([O-])=O.N1C=CC=CC=1>O1CCOCC1>[CH3:1][C:2]1[CH2:24][S:3][C@@H:4]2[C@H:11]([NH:12][C:13](=[O:21])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10](=[O:22])[N:5]2[C:6]=1[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 22764074HCID 22764074, compoundHCID 90473365HCID 90473365, compound

Product 1

HCID 168674Phenylacetyl 7-aminodesacetoxycephalosporanic acidYield 244.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The polymer ester of (1S, 5R, 6R)-2,2-dimethyl-6-phenylacetamidopenam-3-carboxylic acid 1-oxide[45.60g, 0.05 mole, from example 29(a)] was refluxed for 24 hours in dioxan (500 ml.) with trichloroethylphosphate (1.15g, 5.0 m.mole) and pyridine (0.41 ml., 0.40g, 0.0051 mole) as in example 16 above to give the polymer ester of (6R, 7R)-3-methyl-7-phenylacetamidoceph-3-em-4-carboxylic acid (40.65g). The IR and NMR spectra were identical with the product obtained in example 8 above.

Sources & evidence

ORD record
ord-337e2731ce2340cb8933ead5b57a84b1
Source dataset
uspto-grants-1978_01
Patent number
US04067858

Reaction notes

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