Serinol → 5-Chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1-hydroxymethyl-ethyl)-amide

To a stirred solution of 2-amino-1,3-propanediol (0.5 g, 5.49 mmol) in water (2 ml) was added at room temperature magnesium oxide (1.11 g, 27.5 mmol) and THF (6 ml). The suspension was stirred at room temperature for 30 min and a solution of 5-chloro-4-nitrothiophene-2-sulfonyl chloride (2.88 g, 10.9 mmol) in THF (2 ml) was added. The light yellow suspension was stirred at room temperature for 1 h and, after filtration on Dicalit, evaporated. Water (60 ml) was added and the mixture was extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-1-hydroxymethyl-ethyl)-amide (0.76 g, 44%) as a light yellow solid. MS (ISP) 314.9 [(M−H)−], mp 142° C.

1. stirringThe light yellow suspension was stirred at room temperature for 1 h
2. filtrationafter filtration on Dicalit
3. customevaporated
4. additionWater (60 ml) was added
5. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
6. washThe combined organic layers were washed with brine (70 ml)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe crude product was further purified by column chromatography on silica gel (heptane/ethyl acetate 1:1) and subsequent crystallization from ethyl acetate/hexane

ORD record

ord-cc7f0ce942904c4f964f21d8a02faea9

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361659B2