Methanol → Methyl L-tert-leucinate hydrochloride

HRID 1707856Notes

Reaction equation

HRID 1707856 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@H:6]([C:11]([OH:13])=[O:12])[C:7]([CH3:10])([CH3:9])[CH3:8].[CH3:14]O>>[ClH:3].[CH3:14][O:12][C:11](=[O:13])[C@H:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl Chloride2×HCID 164608L-tert-Leucine

Product 1

HCID 16217630Methyl L-tert-leucinate hydrochlorideYield 92%

Procedure

To anhydrous methanol (15 mL) at -20° C. under nitrogen was added thionyl chloride (4 mL) dropwise. The solution was allowed to warm to room temperature and then tert-Leucine (4.00 g) was added. The reaction mixture was warmed at 50° C. for 5 hours, re-cooled to -20° C., and then additional thionyl chloride (3 mL) was added dropwise. The reaction mixture was heated an additional 2.5 hours at 50° C. and then concentrated under reduced pressure and chased twice with methanol (15 mL) to afford an amorphous solid. The solid was triturated with ether to afford the title compound in 92% yield. The 300 MHz 1H NMR spectrum was found to be consistent with the proposed structure. MS (DCI/NH3) m/e 146 (M+H)+.

Workup

  1. temperatureThe reaction mixture was warmed at 50° C. for 5 hours
  2. temperaturere-cooled to -20° C.
  3. temperatureThe reaction mixture was heated an additional 2.5 hours at 50° C.
  4. concentrationconcentrated under reduced pressure
  5. customto afford an amorphous solid
  6. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-5434641090f543c29dcfe34708ca9570
Source dataset
uspto-grants-1994_10
Patent number
US05354866

Reaction notes

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