Benzaldehyde → (S)-N-Benzylglutamic acid

HRID 1277803Notes

Reaction equation

HRID 1277803 reaction equation
[NH2:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>[Pd].O>[CH2:11]([NH:1][C@H:2]([C:8]([OH:10])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 33032L-Glutamic Acid

Product 1

HCID 11107380(S)-N-Benzylglutamic acidYield 46.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 74.5 g (0.5 mol) of L-glutamic acid, 54 g (0.5 mol) of benzaldehyde, 41 g (1.0 mol) of sodium hydroxide, and 1 liter of water was stirred at room temperature for 3 hours. A 5 g portion of 10% palladium on carbon catalyst was added and the mixture hydrogenated for 83 minutes at 51 psig. The catalyst was filtered and the pH of the filtrate was adjusted to 4.2 with 1 N HCl. The solids were filtered, washed with water and dried to give 55.1 g of N-benzyl-L-glutamic acid mp 151°-153° dec., [α]D23 +16° (c4, 1 N HCl). (c 4.1, 1 N HCl). Concentration of the filtrate gave a second crop of 24.9 g, mp 157°-158° dec., [α]D23 +16° (c 4, 1 N HCl).

Workup

  1. waitthe mixture hydrogenated for 83 minutes at 51 psig
  2. filtrationThe catalyst was filtered
  3. filtrationThe solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-75b43a607aeb4352831a8dab6d33e34d
Source dataset
uspto-grants-1981_07
Patent number
US04278681

Reaction notes

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