Methanol → HCID 135744274, compound

HRID 894959Notes

Reaction equation

HRID 894959 reaction equation
[NH2:1][CH:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:13][OH:14]>>[CH:6](=[N:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:5]1[C:13](=[CH:10][CH:2]=[CH:3][CH:4]=1)[OH:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 994Dl-Phenylalanine

Product 1

HCID 135744274HCID 135744274, compound

Procedure

A mixture of 12.4 g (0.075 mol) of DL-phenyl alanine, 15.5 g (0.086 mol) of l-N-methyl ephedrine, 10.5 g (0.086 mol) of salicyl aldehyde and 135 ml of methanol was stirred at room temperature for about 2 hours until dissolution was complete. The solvent was removed under reduced pressure and the oily residue taken up in 170 ml of ethyl acetate. The clear solution was seeded with a crystal of the salt of l-N-methyl ephedrine and N-salicyliden-D-phenyl alanine, whereupon a yellow crystal magma formed after a short stirring at room temperature. The crystals were filtered off immediately and washed with a small amount of ethyl acetate. After drying at 50° C., 6.7 g (40% of the theory) of the salt of l-N-methyl ephedrine and N-salicyliden-D-phenyl alanine having a specific rotation of [α]D20 of +107.4° were obtained.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customformed after
  3. stirringa short stirring at room temperature
  4. filtrationThe crystals were filtered off immediately
  5. washwashed with a small amount of ethyl acetate
  6. customAfter drying at 50° C.

Sources & evidence

ORD record
ord-1298908abae04e6abd86003e555d54fd
Source dataset
uspto-grants-1981_08
Patent number
US04285884

Reaction notes

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