Methanol → HCID 86742519, compound

HRID 2231400Notes

Reaction equation

HRID 2231400 reaction equation
C(OC=CC[S:8]C)(=O)C.CO.[C]=O.[C:14]([O:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=O)(=[O:16])[CH3:15]>O1CCCC1.C1(C)C=CC=CC=1>[C:14]([O:17][CH:18]([CH2:23][CH2:24][S:25][CH3:26])[C:19]([O:21][CH3:22])=[S:8])(=[O:16])[CH3:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 544393541-Acetoxy-3-methylthiopropeneHCID 86132149HCID 86132149, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86742519HCID 86742519, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.5 mmoles 1-acetoxy-3-methylthiopropene, (Z: E ratio 43:57), and 0.5 mmoles methanol were charged into a 71 cc stainless steel bomb equipped with a glass liner and a Teflon coated stir bar. Ten mole percent, based on 1-acetoxy-3methylthiopropene, of a catalyst comprising [(allyl)PdCl]2 plus Pφ3 co-catalyst (200 mole percent) was added. Toluene was included as an internal standard. Five milliliters of tetrahydrofuran as a solvent were also included in the reaction system. The reaction mixture was charged under argon. The bomb was sealed and carbon monoxide at a pressure of 500 psi (at room temperature) was charged to the bomb, and the bomb was heaterd to 100° C. and allowed to react for 44 hours with stirring. At the terminatlon of the reaction, the reaction produrts were analyzed by gas chromatography and it was found that 2-acetoxy-4-(methylthio)butanoic acid, methyl ester was produced in a yield of 1.5 percent, and that 2-acetoxy-4-(methylthio)thiobutanoic acid, methyl ester was produced in a yield of 3 percent, based on the 1-acetoxy-3-methylthiopropene reactant charged. Each of the products is hydrolyzable to methionine hydroxy analog.

Workup

  1. customequipped with a glass liner and a Teflon coated stir bar
  2. additionwas added
  3. additionThe reaction mixture was charged under argon
  4. customThe bomb was sealed
  5. customwas heaterd to 100° C.
  6. customto react for 44 hours
  7. customAt the terminatlon of the reaction
  8. customthe reaction produrts
  9. customwas produced in a yield of 1.5 percent

Sources & evidence

ORD record
ord-dedc187184ee4a66a5c18841832a706d
Source dataset
uspto-grants-1988_11
Patent number
US04782173

Reaction notes

Loading…