Acetic Acid → 7-[2-(2-Aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 745415Notes

Reaction equation

HRID 745415 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([O:20]CC4C=CC([N+]([O-])=O)=CC=4)=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(O)(=O)C.O.CO>[C].[Pd].O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:8]([NH:10][CH:11]2[C:31](=[O:32])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 1317123324-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylate

Product 1

HCID 1317123337-[2-(2-Aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylic acidYield 52.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.7 g.), 10% palladium carbon (1 g.), acetic acid (1 ml.), water (4 ml.), methanol (20 ml.) and tetrahydrofuran (30 ml.) was subjected to catalytic reduction at room temperature under ordinary pressure for 6 hours. After removing the insoluble substance from the resultant mixture by filtration, the filtrate was concentrated in vacuo. Water was added to the residue and adjusted to pH 7 to 8 with sodium bicarbonate, and the insoluble substance was filtered out. The filtrate was washed with ethyl acetate and adjusted to pH 3.0 with conc. hydrochloric acid under ice cooling. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.1 g.).

Workup

  1. customAfter removing the insoluble substance from the resultant mixture
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionWater was added to the residue
  5. filtrationthe insoluble substance was filtered out
  6. washThe filtrate was washed with ethyl acetate
  7. filtrationThe precipitates were collected by filtration
  8. washwashed with water
  9. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-740093541ba043379a806a1ae37e6f62
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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