HCID 86739066, compound → HCID 54270045, compound

HRID 1656173Notes

Reaction equation

HRID 1656173 reaction equation
[C:1]([O:5][C:6](/[CH:8]=[CH:9]/[CH2:10][O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.C(O)C.[Pd].O>[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][O:11][N:12]=[C:13]([C:17]1[N:18]=[C:19]([NH:22][CH:23]=[O:24])[S:20][CH:21]=1)[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 1

HCID 86739066HCID 86739066, compound

Product 1

HCID 54270045HCID 54270045, compoundYield 22.4%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(trans-3-tert-butoxycarbonylallyloxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (8.0 g) in ethyl acetate (60 ml) and ethanol (60 ml) was added 10% palladium on carbon (4.0 g) moistened in water (3 ml) in a stream of nitrogen atmosphere, followed by subjecting to catalytic reduction under atmospheric pressure for 4 hours. After the catalyst was removed by filtration, the filtrate was evaporated. To the residue were added water and ethyl acetate, followed by adjusting to pH 7.5 with a saturated aqueous sodium bicarbonate. The separated aqueous layer was washed with ethyl acetate, and thereto was added ethyl acetate, followed by adjusting to pH 2.0 with 10% hydrochloric acid. The separated organic layer was washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave a residue, which was crystallized from n-hexane and collected by filtration to obtain 2-(3-tert-butoxycarbonylpropoxyimino)-2-(2-formamidothiazol-4yl)acetic acid (syn isomer) (1.80 g).

Workup

  1. customAfter the catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. additionTo the residue were added water and ethyl acetate
  4. washThe separated aqueous layer was washed with ethyl acetate
  5. additionwas added ethyl acetate
  6. washThe separated organic layer was washed with a saturated aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent
  9. customgave a residue, which
  10. customwas crystallized from n-hexane
  11. filtrationcollected by filtration

Sources & evidence

ORD record
ord-84856dcc057447c1a77a8b7e6b972c0c
Source dataset
uspto-grants-1993_10
Patent number
US05252731

Reaction notes

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