Acetic Acid → HCID 131716068, compound

HRID 1723598Notes

Reaction equation

HRID 1723598 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:34]2[N:35]=[C:36]([NH:39][CH:40]=[O:41])[S:37][CH:38]=2)[C:7]([NH:9][C@@H:10]2[C:32](=[O:33])[N:12]3[C:13]([C:19]([O:21]CC4C=CC([N+]([O-])=O)=CC=4)=[O:20])=[C:14]([O:17][CH3:18])[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1.[H][H].O1CCCC1.C(O)(=O)C>[Pd].CO>[CH:1]1([O:4][N:5]=[C:6]([C:34]2[N:35]=[C:36]([NH:39][CH:40]=[O:41])[S:37][CH:38]=2)[C:7]([NH:9][C@@H:10]2[C:32](=[O:33])[N:12]3[C:13]([C:19]([OH:21])=[O:20])=[C:14]([O:17][CH3:18])[CH2:15][S:16][C@H:11]23)=[O:8])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 131716069HCID 131716069, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131716068HCID 131716068, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

p-Nitrobenzyl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylate (syn isomer) (0.9 g) was hydrogenated under 1 atmospheric pressure of hydrogen in the presence of 10% palladium on carbon (0.9 g) in a mixture of methanol (20 ml), tetrahydrofuran (400 ml), and acetic acid (0.01 ml) at ambient temperature for 2 hours. The catalyst was filtered off and washed successively diluted aqueous solution of sodium bicarbonate and tetrahydrofuran. The filtrate and the washings were combined and washed with ethyl acetate. The aqueous solution was adjusted to pH 3 with 1N hydrochloric acid and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo, and triturated in diisopropyl ether to give 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-methoxy-3-cephem-4-carboxylic acid (syn isomer) (0.35 g) as a solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed successively diluted aqueous solution of sodium bicarbonate and tetrahydrofuran
  3. washwashed with ethyl acetate
  4. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  5. washThe extract was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customtriturated in diisopropyl ether

Sources & evidence

ORD record
ord-ffa4501f2c034204ae5ceffdec05ead7
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

Loading…