HCID 70524127, compound → HCID 70524691, compound

HRID 1902516Notes

Reaction equation

HRID 1902516 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[CH:14]([C:20]([O:22][CH:23]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[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>C(O)(=O)C.O1CCCC1.C(O)C.[C].[Pd]>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[C:36](=[O:37])[N:13]3[CH:14]([C:20]([O:22][CH:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)=[O:21])[CH:15]([CH2:18][OH:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 1

HCID 70524127HCID 70524127, compound

Product 1

HCID 70524691HCID 70524691, compoundYield 56.4%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 10% palladium-carbon (30 g.) in acetic acid (300 ml.) was added to a solution of diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethyl-2-cephem-4-carboxylate (30.0 g.) in tetrahydrofuran (500 ml.) and ethanol (100 ml.), and the mixture was subjected to catalytic reduction under hydrogen pressure of 10 kg/cm2 at 50°-55° C. for 4 hours. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was concentrated under reduced pressure. Ethyl acetate (500 ml.) was added to a residue and adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride in turn and dried over magnesium sulfate. The solution was concentrated under reduced pressure to give diphenylmethyl 7-(2-phenylacetamido)-3-hydroxymethylcepham-4-carboxylate (17 g.).

Workup

  1. customat 50°-55° C.
  2. customfor 4 hours
  3. customAfter removing the insoluble substance from the resultant mixture
  4. filtrationby filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionEthyl acetate (500 ml.) was added to a residue
  7. customThe organic layer was separated
  8. washwashed with water
  9. dry with materiala saturated aqueous solution of sodium chloride in turn and dried over magnesium sulfate
  10. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6971a0d2d00940fa9b37ef7a1ae2362a
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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