HCID 131712231, compound → HCID 131712234, compound

HRID 2286643Notes

Reaction equation

HRID 2286643 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[N:34][O:35][CH3:36])[C:9]([NH:11][CH:12]2[C:32](=[O:33])[N:14]3[C:15]([C:19]([O:21]CC4C=CC([N+]([O-])=O)=CC=4)=[O:20])=[CH:16][CH2:17][S:18][C@H:13]23)=[O:10])[N:3]=1>[Pd].O1CCCC1>[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[N:34][O:35][CH3:36])[C:9]([NH:11][CH:12]2[C:32](=[O:33])[N:14]3[C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH2:17][S:18][C@H:13]23)=[O:10])[N:3]=1

Participants

4

Reactant 1

HCID 131712231HCID 131712231, compound

Product 1

HCID 131712234HCID 131712234, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl 7-[2-(4-aminopyrimidin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer) (3.0 g) and 10% palladium on carbon (1.5 g) in 50% aqueous tetrahydrofuran (90 ml) was stirred under hydrogen atmosphere for 3 hours at ambient temperature. The catalyst was removed by filtration and the filtrate was concentrated to half of the original volume. The remaining aqueous solution was diluted with water (100 ml), washed with ethyl acetate, adjusted to pH 3 with 10% hydrochloric acid and subjected to column chromatography over nonionic adsorption resin, "Diaion HP20". The column was washed with water and eluted with 10% methanol. The eluent containing a desired compound was evaporated to remove the methanol in vacuo and then lyophilized to give 7-[2-(4-amino-pyrimidin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer) (750 mg), mp 191°-197° C. (dec.).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to half of the original volume
  3. additionThe remaining aqueous solution was diluted with water (100 ml)
  4. washwashed with ethyl acetate
  5. washThe column was washed with water
  6. washeluted with 10% methanol
  7. additionThe eluent containing a desired compound
  8. customwas evaporated
  9. customto remove the methanol in vacuo

Sources & evidence

ORD record
ord-2a62a39d82a84a80bca598a7f1005ded
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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