Hydrochloric Acid → Leucine, N-carboxy-, N-benzyl ester, L-

HRID 1775750Notes

Reaction equation

HRID 1775750 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12].Cl>[OH-].[Na+]>[CH2:14]([O:13][C:11]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6106L-LeucineHCID 10387Benzyl chloroformate

Product 1

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To the solution of L-leucine (0.400 g, 3.049*10−3 mol) in 2M NaOH aq. (3.75 ml) cooled to 0° C., benzyl chloroformate (3.5374*10−3 mol, 0.52 ml) was added dropwise over 15 min. The mixture was stirred at RT for another 2 h, and then acidified with HCl conc. The aqueous layer was extracted with AcOEt (3×10 ml) and the combined organic layers were dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to give crude N-benzoxycarbonyl-L-leucine. (colourless oil) (76%).

Workup

  1. extractionwas extracted with AcOEt (3×10 ml)
  2. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-0259b9a997ac4ad9be213db47d064493
Source dataset
uspto-grants-2016_02
Patent number
US09260460B2

Reaction notes

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