Formaldehyde → (2S)-2-[benzyl(methyl)amino]propanoic acid

HRID 1722618Notes

Reaction equation

HRID 1722618 reaction equation
[CH2:1]([NH:8][C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]=O>C(O)=O>[CH3:14][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 723764N-benzyl-L-alanine

Product 1

HCID 825998(2S)-2-[benzyl(methyl)amino]propanoic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The N-benzylalanine (1), (67 g, 0.374 mole) was taken up in formic acid (41 mL, 88%) and formaldehyde (37 mL, 38%) added. The resulting solution was heated on a steam bath for 11/2 hours. After this period the clear solution was cooled and as much of the solvent as possible removed under reduced pressure. Removal of the water was aided by co-evaporation with methanol. To the residual oil was added methanol (200 mL) and the solution diluted with ether yielding the product as a fine white powder, 63.7 g (88%).

Workup

  1. temperatureThe resulting solution was heated on a steam bath for 11/2 hours
  2. temperatureAfter this period the clear solution was cooled
  3. customas much of the solvent as possible removed under reduced pressure
  4. customRemoval of the water
  5. additionTo the residual oil was added methanol (200 mL)
  6. additionthe solution diluted with ether yielding the product as a fine white powder, 63.7 g (88%)

Sources & evidence

ORD record
ord-19abd6cebd6646319ae21afeff832679
Source dataset
uspto-grants-1989_08
Patent number
US04857440

Reaction notes

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