Benzaldehyde → N-benzyl D-leucine methyl ester

HRID 355441Notes

Reaction equation

HRID 355441 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH2:6].C([O-])(=O)C.[Na+].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([CH2:7][CH:8]([CH3:10])[CH3:9])[NH:6][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 11600782D-Leucine Methyl Ester Hydrochloride

Product 1

HCID 18666514N-benzyl D-leucine methyl esterYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

D-Leucine methyl ester hydrochloride (35 g, 193 mmol) is dissolved in methanol. To this is added sodium acetate (39.4 g, 480 mmol), followed by benzaldehyde (19.8 mL, 195 mmol). This mixture is stirred for 15 minutes and a solution of sodium cyanoborohydride (7.1 g, 113 mmol) in methanol (50 mL) is added over 15 minutes. After 3 hours the reaction is complete. A 10% aqueous solution of sodium bicarbonate is added with stirring and after 10 minutes the volatiles are removed. The product is extracted with ether and washed with water (2×). The ether mixture is dried over sodium sulfate and evaporated to give 39.9 g of N-benzyl D-leucine methyl ester as a colorless oil.

Workup

  1. waitAfter 3 hours the reaction is complete
  2. stirringwith stirring and after 10 minutes the volatiles
  3. customare removed
  4. extractionThe product is extracted with ether
  5. washwashed with water (2×)
  6. dry with materialThe ether mixture is dried over sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-53d13de2c27b49248af6b7d6656d0793
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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