Methanol → L-Methionine, methyl ester, hydrochloride

HRID 1775745Notes

Reaction equation

HRID 1775745 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].S(Cl)([Cl:12])=O.[CH3:14]O>>[ClH:12].[CH3:14][O:8][C:7](=[O:9])[C@H:2]([CH2:3][CH2:4][S:5][CH3:6])[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 6137L-MethionineHCID 24386Thionyl Chloride

Product 1

HCID 11435579L-Methionine, methyl ester, hydrochlorideYield 98%

Procedure

L-Methionine (0.5 g, 1 equivalent) was suspended in methanol (30 ml C=0.1M) in a 100 ml flask equipped with a magnetic stirrer and placed under nitrogen. Thionyl chloride (0.5 ml, 2 equivalents) was added to the solution dropwise at 0° C. then heated under reflux for 16 hours. The reaction mixture was then evaporated to yield a pale yellow solid. The solid was triturated with hot diethyl ether and the solution discarded to leave the title compound 2′ a white solid which was further dried under vacuum. (0.65561 g, 98% yield).

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturethen heated
  3. temperatureunder reflux for 16 hours
  4. customThe reaction mixture was then evaporated
  5. customto yield a pale yellow solid
  6. customThe solid was triturated with hot diethyl ether

Sources & evidence

ORD record
ord-d9b156954b6d4345b048cb2c749d6a70
Source dataset
uspto-grants-2016_02
Patent number
US09260460B2

Reaction notes

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