Reaction #2186173

Reaction equation

S-(2,3-dihydroxypropyl)cysteine

fluorenylmethoxycarbonyl-N-hydroxysuccinimide

→

powder

Yield 63.8%

N-Fluorenylmethoxycarbonyl-S-(2,3-dihydroxypropyl)cysteine

Yield 63.8%

Solvents

sodium carbonate

acetonitrile

water

Conditions

Workup

1. 1
   Extractionextracted with diethyl ether (25 ml×3)
2. 2
   Extractionwas then extracted with ethyl acetate (70 ml×3)
3. 3
   WashThe extract was washed with water (50 ml×2) and saturated sodium chloride solution (50 ml×2)
4. 4
   Dryingdried over sodium sulfate
5. 5
   Otherevaporated to dryness
6. 6
   OtherRecrystalisation from ether and ethyl acetate at −20° C.

Procedure

S-(2,3-dihydroxypropyl)cysteine (2.45 g, 12.6 mmole) was dissolved in 9% sodium carbonate (20 ml). A solution of fluorenylmethoxycarbonyl-N-hydroxysuccinimide (3.45 g, 10.5 mmole) in acetonitrile (20 ml) was added and the mixture stirred for 2 h, then diluted with water (240 ml), and extracted with diethyl ether (25 ml×3). The aqueous phase was acidified to pH 2 with concentrated hydrochloric acid and was then extracted with ethyl acetate (70 ml×3). The extract was washed with water (50 ml×2) and saturated sodium chloride solution (50 ml×2), dried over sodium sulfate and evaporated to dryness. Recrystalisation from ether and ethyl acetate at −20° C. yielded a colourless powder (2.8 g, 6.7 mmole, 63.8%).

Source