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

HRID 848323Notes

Reaction equation

HRID 848323 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([O:22]CC4C=CC([N+]([O-])=O)=CC=4)=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].O1CCCC1.CO.C(O)(=O)C>[C].[Pd].O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:35][O:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 1317124564-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]3-cephem-4-carboxylate

Product 1

HCID 1317124577-[2-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 68.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 4-nitrobenzyl 7[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 34.5 g.), tetrahydrofuran (345 ml.), 10% palladium carbon (14 g.), methanol (140 ml.), acetic acid (2.5 ml.) and water (50 ml.) was subjected to catalytic reduction under ordinary pressure at room temperature for 3 hours. The resultant mixture was filtered, and washed with tetrahydrofuran. The filtrate was concentrated in vacuo, and the residue was dissolved in a mixture of ethyl acetate and an aqueous solution of sodium bicarbonate. The insoluble substance was removed by filtration. After the ethyl acetate layer was separated and extracted with an aqueous solution of sodium bicarbonate, the aqueous layer and the aqueous extract were combined. After the aqueous solution was washed with ethyl acetate and diethyl ether in turn, the solution was adjusted to pH 2.0 with 10% hydrochloric acid and stirred for 30 minutes. The precipitates were collected by filtration, washed with water and dried over magnesium sulfate to give 7-[2-(2-formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 18.3 g.).

Workup

  1. filtrationThe resultant mixture was filtered
  2. washwashed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was dissolved in a mixture of ethyl acetate
  5. customThe insoluble substance was removed by filtration
  6. customAfter the ethyl acetate layer was separated
  7. extractionextracted with an aqueous solution of sodium bicarbonate
  8. extractionthe aqueous layer and the aqueous extract
  9. washAfter the aqueous solution was washed with ethyl acetate and diethyl ether in turn
  10. filtrationThe precipitates were collected by filtration
  11. washwashed with water
  12. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-22fb5734be274dda9deca848d15ebbef
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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