Hydrochloric Acid → HCID 86742519, compound

HRID 2231396Notes

Reaction equation

HRID 2231396 reaction equation
C(OC=CC[S:8]C)(=O)C.CO.Cl.[C]=O.[C:15]([O:18][CH:19]([CH2:24][CH2:25][S:26][CH3:27])[C:20]([O:22][CH3:23])=O)(=[O:17])[CH3:16]>O1CCCC1.C1(C)C=CC=CC=1>[C:15]([O:18][CH:19]([CH2:24][CH2:25][S:26][CH3:27])[C:20]([O:22][CH3:23])=[S:8])(=[O:17])[CH3:16]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 544393541-Acetoxy-3-methylthiopropeneHCID 86132149HCID 86132149, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86742519HCID 86742519, compoundYield 17.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

0.5 mmoles 1-acetoxy-3-methylthiopropene, (Z: E ratio 43:57), and 2.5 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-3-methylthiopropene, of a catalyst comprising Pd(Pφ3)4 plus 10 mole percent HCl co-catalyst 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 1000 psi (at room temperature) was charged to the bomb, and the bomb was heated to 100° C. and allowed to react for 45.25 hours with stirring. At the termination of the reaction, the reaction products were analyzed by gas chromatography and it was found that 2-acetoxy-4-(methylthio)butanoic acid, methyl ester was produced in a yield of 21.7 percent, and that 2-acetoxy-4-(methylthio)thiobutanoic acid, methyl ester was produced in a yield of 17.8 percent, based on the 1-acetoxy-3-methylthiopropene reactant charged. Note that each of the products is hydrolyzable to methionine hydroxy analog. When this run was repeated without the HCl co-catalyst (run length 44 hours), the yields of the above ester and thioester were3 93 percent.and 4.48 percent, respectively.

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. customto react for 45.25 hours
  6. customAt the termination of the reaction
  7. customwas produced in a yield of 21.7 percent

Sources & evidence

ORD record
ord-1293bb62fa9f469493715ce2807a7298
Source dataset
uspto-grants-1988_11
Patent number
US04782173

Reaction notes

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