Acetic Acid → HCID 131712010, compound

HRID 1758064Notes

Reaction equation

HRID 1758064 reaction equation
[O:1]1[C:6]([C:7](=[N:33][O:34][CH3:35])[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])=[CH:5][S:4][CH2:3][CH2:2]1.CO.O.C(O)(=O)C>O1CCCC1.[C].[Pd]>[O:1]1[C:6]([C:7](=[N:33][O:34][CH3:35])[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])=[CH:5][S:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 131712011HCID 131712011, compound

Product 1

HCID 131712010HCID 131712010, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Thus obtained 4-nitrobenzyl 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 3.30 g.) was suspended in a mixture of tetrahydrofuran (150 ml.), methanol (70 ml.), water (10 ml.) and acetic acid (1 ml.). 10% Palladium carbon (2.3 g.) was added to the solution, and subjected to catalytic reduction at room temperature for 45 minutes. After removing the catalyst from the resultant solution by filtration, the filtrate was concentrated in vacuo. Water and a saturated aqueous solution of sodium bicarbonate were added to the residue and adjusted to pH 7.0. After filtration, the filtrate was washed with ethyl acetate (60 ml.) and methylene chloride (20 ml.), and then the organic solvent was removed by introducing nitrogen gas. The solution was adjusted to pH 2.0 with 10% hydrochloric acid under ice cooling. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2,3-dihydro-1,4-oxathiin-6-yl)-2-methoxyiminoacetamido] -3-cephem-4-carboxylic acid (syn isomer, 1.55 g.).

Workup

  1. customAfter removing the catalyst from the resultant solution
  2. filtrationby filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionWater and a saturated aqueous solution of sodium bicarbonate were added to the residue
  5. filtrationAfter filtration
  6. washthe filtrate was washed with ethyl acetate (60 ml.) and methylene chloride (20 ml.)
  7. customthe organic solvent was removed
  8. additionby introducing nitrogen gas
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with water
  11. customdried

Sources & evidence

ORD record
ord-ee4b74827c584657b97a481b7c024954
Source dataset
uspto-grants-1983_02
Patent number
US04371531

Reaction notes

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