Methanesulfonic Acid → HCID 61142891, compound

HRID 1904158Notes

Reaction equation

HRID 1904158 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH3:13])[NH:5][C:6](=[O:12])/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10].NC(N)=S.CS(O)(=O)=O>C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C@H:4]([CH3:13])[NH:5][C:6](=[O:12])/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 2723790ThioureaHCID 86743092HCID 86743092, compound

Product 1

HCID 61142891HCID 61142891, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

This compound was isomerized to the fumaryl amide ester by the following procedure. (Z)-N-(3-Carboxy-1-oxo-2-propenyl) -L-alanine methyl ester (67.5 g.) was mixed with 1.28 g. thiourea and 2.18 ml. anhydrous methanesulfonic acid in 675 ml. dry ethyl acetate. The mixture was stirred at reflux for one hour and cooled to 25° C. After addition of 500 ml. water, the organic layer was separated and dried over anhydrous sodium sulphate. The solution was filtered and the solvent distilled under vacuum of 1-2 mm Hg leaving a solid residue that was dried to constant weight affording 50.1 g (74.2% yield) of the (E)N-(3-carboxy-1-oxo-2-propenyl)-L-alanine methyl ester. The NMR in d6 -dimethyl sulfoxide showed the product to be free of the Z-isomer.

Workup

  1. temperatureat reflux for one hour
  2. additionAfter addition of 500 ml
  3. customwater, the organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationThe solution was filtered
  6. distillationthe solvent distilled under vacuum of 1-2 mm Hg
  7. customleaving a solid residue that
  8. customwas dried to constant weight

Sources & evidence

ORD record
ord-75ee995e07564178bedaaa8d0a4b94fd
Source dataset
uspto-grants-1989_06
Patent number
USH0000645

Reaction notes

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