Triethylamine → L-Leucine

A solution containing L-leucine methyl ester hydrochloride (2.9 g, 16 mmol), 2-bromo-1,1-dimethoxy ethane (1.9 ml, 2.7 g, 16 mmol), NEt3 (6.7 ml, 48 mmol) and a catalytic amount of KI in DMF (190 ml) was stirred at 120° C. for 3 days. The reaction mixture was concentrated under reduced pressure, diluted with water and extracted with DCM. The organic layer was then washed with brine, dried over Na2SO4 and evaporated. The crude product was purified by column chromatography (silica gel, EtOAc/P.E. 1:1) to afford compound of formula (III), where R=Leu side chain, as a yellow oil (1.2 g, 32% yield).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additiondiluted with water
3. extractionextracted with DCM
4. washThe organic layer was then washed with brine
5. dry with materialdried over Na2SO4
6. customevaporated
7. customThe crude product was purified by column chromatography (silica gel, EtOAc/P.E. 1:1)

ORD record

ord-55567e661dcb4205aafe5ec8a22e8489

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08445484B2