Water → 7-[2-(6-Formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1982662Notes

Reaction equation

HRID 1982662 reaction equation
[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:36][O:37][CH3:38])[C:11]([NH:13][CH:14]2[C:34](=[O:35])[N:16]3[C:17]([C:21]([O:23]CC4C=CC([N+]([O-])=O)=CC=4)=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2].O>[Pd].O1CCCC1.CO.C(O)(=O)C>[CH:1]([NH:3][C:4]1[N:9]=[C:8]([C:10](=[N:36][O:37][CH3:38])[C:11]([NH:13][CH:14]2[C:34](=[O:35])[N:16]3[C:17]([C:21]([OH:23])=[O:22])=[CH:18][CH2:19][S:20][C@H:15]23)=[O:12])[CH:7]=[CH:6][CH:5]=1)=[O:2]

Participants

7

Reactant 2

HCID 962WaterHCID 1317122194-Nitrobenzyl 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317122227-[2-(6-Formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 74.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

10% Palladium on carbon (216 mg.) was added to a solution of 4-nitrobenzyl 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (540 mg.) in tetrahydrofuran (10 ml.), methanol (5 ml.), acetic acid (0.075 ml.), and water (0.75 ml.). The mixture was subjected to catalytic reduction at ambient temperature under ordinary pressure for 5 hours, and then allowed to stand overnight. After filtered off the catalyst, the filtrate was concentrated under reduced pressure. Ethyl acetate and an aqueous solution of sodium bicarbonate were added to the residue, and the aqueous layer was separated. The solution was adjusted to pH 2 with 10% hydrochloric acid. The appeared precipitates were collected by filtration, washed with water and dried to give 7-[2-(6-formamidopyridin-2-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (300 mg.), mp. 202° to 204° C. (dec.).

Workup

  1. waitto stand overnight
  2. filtrationAfter filtered off the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate and an aqueous solution of sodium bicarbonate were added to the residue
  5. customthe aqueous layer was separated
  6. customThe appeared precipitates
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-5b5a971bff77480e9d9840263b9c5ad4
Source dataset
uspto-grants-1986_06
Patent number
US04596869

Reaction notes

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