Ethanol → HCID 54196860, compound

HRID 325972Notes

Reaction equation

HRID 325972 reaction equation
[NH2:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(O)C.[CH:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=O)[C:25]([OH:27])=[O:26])[N:23]=1)=[O:17].[OH-].[Na+]>O1CCCC1.CCCCCC.O>[C:9]([O:8][C:6]([CH:5]=[CH:4][CH2:3][O:2][N:1]=[C:24]([C:22]1[N:23]=[C:19]([NH:18][CH:16]=[O:17])[S:20][CH:21]=1)[C:25]([OH:27])=[O:26])=[O:7])([CH3:12])([CH3:11])[CH3:10]

Participants

8

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 13116693(2-Formamido-1,3-thiazol-4-yl)(oxo)acetic acidHCID 19790226HCID 19790226, compound

Product 1

HCID 54196860HCID 54196860, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

To tert-butyl 4-aminooxycrotonate (10.0 g) were added ethanol (150 ml) and water (150 ml), followed by gradually adding (2-formamidothiazol-4-yl)glyoxylic acid (11.0 g) with stirring. During the addition, the mixture was adjusted to pH 5 to 5.5 with 10% aqueous sodium hydroxide, and the stirring was continued at ambient temperature for 2 hours. After removal of the ethanol, to the remaining aqueous solution was added ethyl acetate, followed by adjusting to pH 7.5 with 10% aqueous sodium hydroxide. The aqueous layer was separated and washed with ethyl acetate. Thereto was further 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 pulverized with n-hexane and tetrahydrofuran, and collected by filtration. To this substance were added ethanol (50 ml) and water (30 ml), followed by adjusting to pH 7.5 with 10% aqueous sodium hydroxide. The precipitated substance was collected by filtration, washed with a mixed solvent of water and ethanol (1:1 by volume), followed by addition of water and ethyl acetate, and adjusting to pH 2.0 with 10% hydrochloric acid. The organic layer was separated, washed with a saturated aqueous sodium chloride and then dried over magnesium sulfate. Removal of the solvent gave a residue, which was pulverized with n-hexane and tetrahydrofuran to obtain 2-(3-t-butoxycarbonyl-2-propenyloxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer) (12.01 g).

Workup

  1. additionDuring the addition
  2. customAfter removal of the ethanol
  3. additionto the remaining aqueous solution was added ethyl acetate
  4. customThe aqueous layer was separated
  5. washwashed with 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. filtrationcollected by filtration
  11. additionTo this substance were added ethanol (50 ml) and water (30 ml)
  12. filtrationThe precipitated substance was collected by filtration
  13. washwashed with a mixed solvent of water and ethanol (1:1 by volume)
  14. additionfollowed by addition of water and ethyl acetate
  15. customThe organic layer was separated
  16. washwashed with a saturated aqueous sodium chloride
  17. dry with materialdried over magnesium sulfate
  18. customRemoval of the solvent
  19. customgave a residue, which

Sources & evidence

ORD record
ord-f9c58b92e15e470880666e729e66e027
Source dataset
uspto-grants-1984_04
Patent number
US04443444

Reaction notes

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