Réaction #56706

Équation de réaction

LiCl

(R)-4-methyl-heptanoic acid

triethylamine

trimethylacetylchloride

(4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone

→

(4R,5S)-4-methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrewas removed by filtration
2. 2
   Concentrationthe solution concentrated under reduced pressure

Mode opératoire

To (R)-4-methyl-heptanoic acid (19 g, 0.132 mol) and triethylamine (49.9 g, 0.494 mol) in THF (500 mL) at 0° C. was added trimethylacetylchloride (20 g, 0.17 mol). After 1 hour LiCl (7.1 g, 0.17 mol) was added followed by (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone) 3 (30 g, 0.17 mol). The mixture was warmed to room temperature and after 16 hours the filtrate was removed by filtration and the solution concentrated under reduced pressure. Flash chromatography (7:1 hexane/EtOAc) gave (4R,5S)-4-methyl-3-((R)-4-methyl-heptanoyl)-5-phenyl-oxazolidin-2-one as an oil. 31.5 g; 79%. [a]D=+5.5 (c 1 in CHCl3). MS, m/z (relative intensity): 304 [M+H, 100%].

Source