Reaction #344289

Reaction equation

di-t-butyl azodicarboxylate

(3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone

triphenylphosphine

salicylamide

→

o-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-benzamide

Yield 49.5%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureAfter warming to room temperature
2. 2
   Concentrationwas concentrated
3. 3
   Otherthe residue was partitioned between methanol/water (70:30) and hexane
4. 4
   Extractionextracted with hexane
5. 5
   DryingThe hexane phase was dried
6. 6
   Concentrationconcentrated
7. 7
   Otherthe residue was chromatographed on silica gel with hexane/ethyl acetate (4:1)

Procedure

1.1 g of (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone, 1.6 g of triphenylphosphine, 0.825 g of salicylamide and 3 g of molecular sieve (4 Å) were treated with 20 ml of THF and cooled to 0° C. Thereupon, 1.4 g of di-t-butyl azodicarboxylate were added. After warming to room temperature and stirring the reaction mixture was concentrated and the residue was partitioned between methanol/water (70:30) and hexane and extracted with hexane. The hexane phase was dried and concentrated and the residue was chromatographed on silica gel with hexane/ethyl acetate (4:1). There were obtained 0.727 g of o-[[(S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl]oxy]-benzamide, MS: 474 (M+H)+.

Source