Methanol → Methyl L-tert-leucinate hydrochloride

HRID 742919Notes

Reaction equation

HRID 742919 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-d8c688c705ba48f29a4360840053e35f
Source dataset
uspto-grants-1996_09
Patent number
US05554783

Reaction notes

Loading…