Methanol → Methyl L-tert-leucinate hydrochloride

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)+.

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

ORD record

ord-a78fa28143314d1a9d81106a137a5de2

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05597926