7-Phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid p-nitrobenzylester → HCID 70361018, compound

HRID 65776Notes

Reaction equation

HRID 65776 reaction equation
[N+](C1C=CC(C[O:9][C:10]([CH:12]2[N:17]3[C:18](=[O:31])[CH:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH2:14][C:13]2([Cl:33])[CH3:32])=[O:11])=CC=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[O:23]([CH2:22][C:21]([NH:20][CH:19]1[C:18](=[O:31])[N:17]2[CH:12]([C:10]([OH:11])=[O:9])[C:13]([Cl:33])([CH3:32])[CH2:14][S:15][C@H:16]12)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 703611517-Phenoxyacetoamido-3-chloro-3-methyl-cepham-4-carboxylic acid p-nitrobenzylesterHCID 178418361HCID 178418361, compound

Product 1

HCID 70361018HCID 70361018, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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:

Workup

  1. filtrationAfter the catalyst was filtered off from the reaction mixture
  2. extractionthe filtrate was extracted with 50 ml of 2% aquous sodium hydrogencarbonate solution
  3. customAfter the aqueous layer was separated
  4. additionby adding diluted hydrochloric acid
  5. extractionthe aqueous layer was extracted again with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. customdried
  8. distillationdistilled under reduced pressure
  9. customThere was obtained

Sources & evidence

ORD record
ord-a1ed53ccdec14293a622bbb246a47235
Source dataset
uspto-grants-1978_12
Patent number
US04128714

Reaction notes

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