Acetic Acid → 7-[2-(2-Amino-4-thiazolyl)-2-ethoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 364532Notes

Reaction equation

HRID 364532 reaction equation
O.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:34][O:35][CH2:36][CH3:37])[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:7]=1.CO.C(O)(=O)C>[Pd].O1CCCC1>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:34][O:35][CH2:36][CH3:37])[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:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 131712451HCID 131712451, compound

Product 1

HCID 1317130207-[2-(2-Amino-4-thiazolyl)-2-ethoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (1.0 g.) moistened with water (3 ml.) was added to a solution of 4-nitrobenzyl 7-[2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.3 g.) in a mixture of tetrahydrofuran (30 ml.), methanol (15 ml.) and acetic acid (0.3 ml.), and the suspension was subjected to catalytic reduction at room temperature under ordinary pressure for 2 hours. After removing the catalyst from the resultant mixture by filtration, the filtrate was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the solution was adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. After removing the insoluble substance by filtration, the aqueous solution was separated, washed with ethyl acetate, adjusted to pH 5.5 and then treated with activated charcoal. The aqueous solution was adjusted to pH 3.2, and the precipitates were collected by filtration and dried to give 7-[2-(2-amino-4-thiazolyl)-2-ethoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.6 g.).

Workup

  1. customAfter removing the catalyst from the resultant mixture
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. customAfter removing the insoluble substance
  6. filtrationby filtration
  7. customthe aqueous solution was separated
  8. washwashed with ethyl acetate
  9. additiontreated with activated charcoal
  10. filtrationthe precipitates were collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-76ff834c5df7405fb1052b3e95eba473
Source dataset
uspto-grants-1986_08
Patent number
US04604456

Reaction notes

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