(+-)-Methionine → HCID 21838360, compound

HRID 1740291Notes

Reaction equation

HRID 1740291 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([O:9]C)[CH:8]=1.NC(C(O)=O)CCSC>CS(O)(=O)=O>[OH:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([OH:9])[CH:8]=1

Participants

4

Reactant 2

HCID 876(+-)-MethionineHCID 21838000HCID 21838000, compound

Product 1

HCID 21838360HCID 21838360, compound

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of methyl 3-(3,5-dimethoxyphenyl)benzoate (0.83 g) and d,l-methionine (9.10 g) in methanesulfonic acid (19.8 ml) was stirred at 40° C. for 10 hours. The mixture was poured onto ice-water and then the product was extracted with ethyl acetate and washed with sodium hydrogencarbonate solution and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (5:1). The fractions containing the desired product was collected and evaporated in vacuo to give methyl 3-(3,5-dihydroxyphenyl)benzoate.

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionthe product was extracted with ethyl acetate
  3. washwashed with sodium hydrogencarbonate solution and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and acetone (5:1)
  7. additionThe fractions containing the desired product
  8. customwas collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-0a4ae07777794a51a8250dca95f6fbbd
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

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