Methanol → D-Leucine Methyl Ester Hydrochloride

HRID 355440Notes

Reaction equation

HRID 355440 reaction equation
[NH2:1][C@@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7](=[O:9])[C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 439524D-Leucine

Product 1

HCID 11600782D-Leucine Methyl Ester Hydrochloride

Conditions

Temperature
0 °C

Procedure

D-leucine (43.63 g, 333 mmol) is dissolved in methanol (400 mL) and cooled to 0° C. To this is added dropwise thionyl chloride (25.5 mL, 350 mmol). The reaction is allowed to stir 16 hours at room temperature at which time the volatiles are removed to give an off-white solid. The product is recrystallized from ethyl acetate/methanol to give D-leucine methyl ester hydrochloride as a fluffy white solid.

Workup

  1. customare removed
  2. customto give an off-white solid
  3. customThe product is recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-7af7741ecc724f75b3bbfda988fe5677
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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