Reaction #94054

Reaction equation

7-phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid p-nitrobenzylester

hydrogen

→

7-phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid

Yield 51.5%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   FiltrationAfter the catalyst was filtered off from the reaction mixture
2. 2
   Extractionthe filtrate was extracted with 50 ml of 2% aquous sodium hydrogencarbonate solution
3. 3
   OtherAfter the aqueous layer was separated
4. 4
   workup.ADDITIONby adding diluted hydrochloric acid
5. 5
   Extractionthe aqueous layer was extracted again with ethyl acetate
6. 6
   WashThe ethyl acetate layer was washed with water
7. 7
   Otherdried
8. 8
   workup.DISTILLATIONdistilled under reduced pressure
9. 9
   OtherThere was obtained

Procedure

In 30 ml of ethyl acetate was dissolved 470 mg of 7-phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid p-nitrobenzylester. To the solution was added 470 mg of 5% palladium-charcoal and the solution was stirred for 19 hours in a stream of hydrogen. After the catalyst was filtered off from the reaction mixture, the filtrate was extracted with 50 ml of 2% aquous sodium hydrogencarbonate solution. After the aqueous layer was separated and adjusted to pH 2 by adding diluted hydrochloric acid, the aqueous layer was extracted again with ethyl acetate. The ethyl acetate layer was washed with water, dried and distilled under reduced pressure. There was obtained 179 mg of 7-phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid as a colourless powder (yield, 15%). The following NMR spectra agreed with those expected from the anticipated structure:

Source