L-Leucine → Leucine methyl ester hydrochloride

HRID 2206971Notes

Reaction equation

HRID 2206971 reaction equation
O=S(Cl)[Cl:3].[OH-].[Na+].[NH2:7][C@H:8]([C:13]([OH:15])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11].[CH:16]1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>C(O)C.CO>[ClH:3].[CH3:16][O:14][C:13](=[O:15])[C@H:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[NH2:7]

Participants

7

Reactant 4

HCID 6106L-LeucineHCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 24386Thionyl Chloride

Product 1

HCID 2723695Leucine methyl ester hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
66 °C

Procedure

Under ice bath, 100 ml round-bottom flask was added with 60 ml of methanol, and then slowly added with 4 ml of SOCl2 through constant pressure dropping funnel (with a drying tube on the top), and NaOH solution was used to absorb exhaust. After stirring for 1 h, 8 mmol of L-leucine was added and stirred at room temperature for 30 min, and then refluxed at 66° C. for 6 h. The reaction was tracked by TLC until the raw material disappears, with a solution of 2% ninhydrin in ethanol as chromogenic reagent. The solvent was evaporated out to obtain L-leucine methyl ester hydrochloride. Yield: 100%.

Workup

  1. customto absorb exhaust
  2. stirringstirred at room temperature for 30 min
  3. customThe solvent was evaporated out

Sources & evidence

ORD record
ord-7163f49bb58946a58f77ae714824f7cc
Source dataset
uspto-grants-2016_06
Patent number
US09376382B2

Reaction notes

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