Reaction #476539

Reaction equation

( 10 )

[(1-Isobutanoyloxyethoxy)carbonyloxy]Succinimide

N-hydroxysuccinimide

compound ( 8 )

O-(1-Isobutanoyloxyethyl) S-tert-Butyl Thiocarbonate

m-Chloroperbenzoic acid

→

title compound ( 10 )

[(1-Isobutanoyloxyethoxy)carbonyloxy]Succinimide

m-chlorobenzoic acid

Solvents

ether

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   workup.ADDITIONwas added over a period of 10 min
3. 3
   Washwashed with water (2×10 mL), saturated sodium bicarbonate solution (10 mL) and brine (10 mL)
4. 4
   DryingThe organic layer was dried over anhydrous sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo

Procedure

In still another alternative synthesis of (10), N-hydroxysuccinimide (230 mg, 2 mmol) was added to a solution of compound (8) (248 mg, 1 mmol) in CH2Cl2 (10 mL) was added and the reaction mixture cooled to 0° C. m-Chloroperbenzoic acid (670 mg, 3 mmol, commercial grade: 77% in water) was added over a period of 10 min and the mixture allowed to stir at room temperature for 16 h. The reaction mixture was diluted with ether (50 mL) and washed with water (2×10 mL), saturated sodium bicarbonate solution (10 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the title compound (10) together with m-chlorobenzoic acid. The crude product mixture was purified by column chromatography on silica gel, eluting with 4:6 EtOAc:hexane. Residual m-chlorobenzoic acid was removed by repeated crystallizations from a mixture of tert-butyl methyl ether and hexane which resulted in analytically pure product (30 mg, 11%).

Source