HCID 70524001, compound → HCID 70523673, compound

HRID 1902508Notes

Reaction equation

HRID 1902508 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[CH:14]([C:20]([OH:22])=[O:21])[C:15]([CH2:18][OH:19])=[CH:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)(=O)C.O.[C].[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:23](=[O:24])[N:13]3[CH:14]([C:20]([OH:22])=[O:21])[CH:15]([CH2:18][OH:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 70524001HCID 70524001, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70523673HCID 70523673, compoundYield 73.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A suspension of palladium carbon (20 g.) in acetic acid (50 ml.) was added to a solution of 7-(2-phenylacetamido)-3-hydroxymethyl-2-cephem-4-carboxylic acid (19.0 g.) in acetic acid (150 ml.) and water (50 ml.). The solution was subjected to catalytic reduction in the presence of hydrogen gas of 20 kg./cm2 at 70° C. for 5 hours. After filtration, the filtrate was concentrated in vacuo. The residue was dissolved in aqueous solution of sodium bicarbonate, washed with ethyl acetate, adjusted to pH 3.0 and then extracted with ethyl acetate. The extract was washed with aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylic acid (14 g.).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in aqueous solution of sodium bicarbonate
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-c618e7bfd8524c869c6ee4cd0e8659c2
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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