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DL-leucine → Methyl DL-leucinate hydrochloride

HRID 85361
Notes
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Reaction equation

HRID 85361 reaction equation
[NH2:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].Cl.[CH3:11]O>>[NH2:1][CH:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH3:11])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 857DL-leucineHCID 21893726Hydrochloride methanol

Product 1

HCID 410817Methyl DL-leucinate hydrochlorideYield 96%

Procedure

2-Amino-4-methylpentanoic acid (5.0 g 38.2 mmol) was slowly added to saturated HCl/MeOH (50 mL). The mixture was stirred (RT, 5 h) then heated to reflux (16 h). After the reaction, the solvent was removed under reduced pressure. The residue was diluted with water (50 mL), then NaHCO3 was added to adjust to pH 7. The mixture was then extracted with DCM (3×50 mL), the combined organic layers were dried over MgSO4, concentrated under reduced pressure to afford methyl 2-amino-4-methylpentanoate as a colorless liquid (5.3 g, 96%). Mass calculated for C7H15NO2=145.20; found: [M+H]+=145.9. The product was used in next step without further purification.

Workup

  1. temperaturethen heated
  2. temperatureto reflux (16 h)
  3. customAfter the reaction
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes
  • customthe solvent was removed under reduced pressure
  • additionThe residue was diluted with water (50 mL)
  • additionNaHCO3 was added
  • extractionThe mixture was then extracted with DCM (3×50 mL)
  • dry with materialthe combined organic layers were dried over MgSO4
  • concentrationconcentrated under reduced pressure
  • Sources & evidence

    ORD record
    ord-cadce66a295947a495f75cef7e9b79a9
    Source dataset
    uspto-grants-2014_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US08846972B2

    Reaction notes

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