L-Methionine → HCID 15617493, compound

HRID 1087341Notes

Reaction equation

HRID 1087341 reaction equation
[CH2:1]([O:12][C:13]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][C:14]=1[CH:15]=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].N[C@H](C(O)=O)CCSC>CS(O)(=O)=O.C(OCC)(=O)C>[CH2:1]([O:12][C:13]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:14]=1[CH:15]=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 6137L-MethionineHCID 15617492HCID 15617492, compound

Product 1

HCID 15617493HCID 15617493, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The 2-undecyloxy-5-methoxybenzaldehyde (16.2 g, 52.9 mmoles) in 100 ml of methanesulfonic acid was treated with L-methionine (16 g, 0.1057 mole) at room temperature for 48 hours. The reaction mixture was diluted with ethyl acetate and washed with ice-cold water and saturated sodium chloride solution. The organic extract was dried with anhydrous magnesium sulfate, treated with charcoal and the solvent was removed in vacuo. The resulting solid was recrystallized twice from hexane to give 7.7 g (50%) of the product as a white solid, mp 66°-67° C.

Workup

  1. washwashed with ice-cold water and saturated sodium chloride solution
  2. extractionThe organic extract
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. additiontreated with charcoal
  5. customthe solvent was removed in vacuo
  6. customThe resulting solid was recrystallized twice from hexane

Sources & evidence

ORD record
ord-5fc3646fd20044359f11365df49e4bd2
Source dataset
uspto-grants-1991_07
Patent number
US05034537

Reaction notes

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