Reaction #632033

Reaction equation

compound ( 2 )

O-(1-Isobutanoyloxyethyl) S-Methyl Thiocarbonate

N-hydroxysuccinimide

peracetic acid

acetic acid

→

title compound ( 17 )

[(1-Isobutanoyloxyethoxy)carbonyloxy] Succinimide

Solvents

ether

CH2Cl2

Conditions

Workup

1. 1
   Washwashed with water (2×10 mL), saturated sodium bicarbonate solution (10 mL) and brine (10 nm)
2. 2
   Dryingdried over anhydrous sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo

Procedure

To a solution of compound (2) (1 g, 4.8 mmol) in CH2Cl2 (10 mL) was added N-hydroxysuccinimide (1.1 g, 9.5 mmol) and the reaction mixture cooled to 0° C. A solution of 32% (v/v) peracetic acid in acetic acid (3.4 mL, 1.1 g, 14.4 mmol) was added dropwise over a period of 10 min, then the solution allowed to stir at room temperature for 3 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 nm), then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give the title compound (17) as a as colorless oil (1 g, 77% yield). After trituration with hexane (20 mL) the product solidified to a white solid. m.p: 50-54° C. 1H NMR (CDCl3, 400 MHz): δ 1.17 (d, J=6.8 Hz, 6H), 1.56 (d, J=5.6 Hz, 3H), 2.55 (m, 1H), 2.82 (s, 4H), 6.80 (q, J=5.2 Hz, 1H). MS (ESI) m/z 296.4 (M+Na)+.

Source