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Acylation of D- and DL-WV with phenoxyacetyl chloride, followed by cleavage of the t-butyl ester,afforded the penultimate penicilloic acids. Phenoxyacetyl chloride was used in the synthesis of series of macrocyclic bis-β-lactams, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester, N-protected guanosine derivatives, useful in RNA synthesis, phenyloxyketene, for cycloaddition to imines leading to β-lactams. Treatment of iminophosphoranes with phenoxyacetyl chloride afforded respectively the trans- and cis-3-(acylamino)-p-lactams. By the oxidative addition of stannous fluoride to allyliodide, with 1, 2-O-isopropylidene-D-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-D-ribose. The 4-disubstituted P-lactams (4a-c and 6a-b) were prepared through the reaction of N,N-diphenylhydrazones and N-methyl-N-phenylhydrazones of ketones with phenoxyacetyl chloride/Et3N in dichloromethane.
Ajay K. Bose,; J. C. Kapur,; J. L. Fahey,; M. S. Manhas. Lactams. XXIX. Synthesis of aza analogs of cepham . J. Org. Chem., . 1973, 38(19), 3437-3438.
John C. Sheehan,; Kenneth R. Henery-Logan. The Total Synthesis of Penicillin V. J. Am. Chem. Soc., 1959, 81(12), 3089-3094.
Can be used to protect OH groups. The phenoxyacetate group is 50x more labile to aqueous ammonia than acetate: Tetrahedron Lett., 4273 (1968). It can also be cleaved with methanolic t-BuNH 2 : Chem. Lett., 965 (1982).
Hazard Statements: H314-H318
Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.