L-Leucine → Benzoyl-L-leucine

HRID 4495

Reaction equation

HRID 4495 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[NH2:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16]>O>[C:1]([NH:12][C@H:13]([C:18]([OH:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6106L-LeucineHCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 853887Benzoyl-L-leucine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzoyl chloride (4.22 g, 0.030 mol) and 10% NaOH (12 ml, 0.030 mol) were added separately with vigorous stirring to a solution of L-leucine (3.94 g, 0.030 mol) in 150 ml of distilled water at ice bath temperature. The reaction was allowed to proceed at this temperature until the reaction mixture became clear (30 minutes); it was then extracted with ethyl acetate (2×100 ml). The aqueous layer was separated, acidified to pH 2 with 10% HCl, and extracted with ethyl acetate (3×50 ml). The ethyl acetate extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated in vacuo to yield quantitative amount of N-benzoyl-L-leucine as a semi-solid which was used directly for the following step.

Workup

  1. custom(30 minutes)
  2. extractionit was then extracted with ethyl acetate (2×100 ml)
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-5d935ab7acac4024b0d5a2228ef4a134
Source dataset
uspto-grants-1988_02
Patent number
US04726941

Linked notes

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