Methanol → 7-[2-(2-Formamidothiazol-4-yl)-2-n-propoxyiminoacetamido)-3-chloro-3-cephem-4-carboxylic acid

HRID 1650520Notes

Reaction equation

HRID 1650520 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:36][O:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:21]([O:23]CC4C=CC([N+]([O-])=O)=CC=4)=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2].CO.O>[C].[Pd].O1CCCC1>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:36][O:37][CH2:38][CH2:39][CH3:40])[C:10]([NH:12][CH:13]2[C:34](=[O:35])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 962WaterHCID 1317124674-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

Product 1

HCID 1317124687-[2-(2-Formamidothiazol-4-yl)-2-n-propoxyiminoacetamido)-3-chloro-3-cephem-4-carboxylic acidYield 85.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 2.4 g.), 10% palladium carbon (1.0 g.), methanol (24 ml.), water (3.6 ml.) and tetrahydrofuran (48 ml.) was subjected to catalytic reduction under ordinary pressure at room temperature. After removing insoluble substance by filtration, the filtrate was concentrated in vacuo. Water and ethyl acetate were added to the residue, and adjusted to pH 8 with a saturated aqueous solution of sodium bicarbonate. The insoluble substance was removed by filtration, and the aqueous layer was separated. Ethyl acetate was added to the solution, adjusted to pH 2.0 with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution and extract were combined together, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo, and the residue was triturated with diethyl ether and collected by filtration to give 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).

Workup

  1. customwas subjected to catalytic reduction under ordinary pressure at room temperature
  2. customAfter removing insoluble substance
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionWater and ethyl acetate were added to the residue
  6. customThe insoluble substance was removed by filtration
  7. customthe aqueous layer was separated
  8. additionEthyl acetate was added to the solution
  9. extractionextracted with ethyl acetate
  10. extractionThe ethyl acetate solution and extract
  11. washwashed with a saturated aqueous solution of sodium chloride
  12. dry with materialdried over magnesium sulfate
  13. concentrationThe solution was concentrated in vacuo
  14. customthe residue was triturated with diethyl ether
  15. filtrationcollected by filtration

Sources & evidence

ORD record
ord-1d56ab5179b84a77aee2cc08a184595a
Source dataset
uspto-grants-1990_05
Patent number
US04923998

Reaction notes

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