Sodium Thiosulfate → HCID 12140789, compound

To a solution of ethyl N-(tert-butoxycarbonyl)-3-(3-hydroxybutylamino)propionate (1.06 g, 3.66 mmol) in dichloromethane (DCM)(15 mL) was added Dess-Martin periodinate (1.17 g, 4.03 mmol). The mixture was stirred for 2 hours, then, a mixture of a saturated aqueous NaHCO3 solution and Na2S2O3 was added. The organic layer was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was dissolved in THF (10 mL), then a Wittig reagent, which was prepared from methyltriphenylphosphonium bromide (1.57 g, 4.4 nmmol) and 1N-tert-BuOK solution in THF (4.4 mL), in THF (10 mL) was added to the solution at 0° C. The mixture was stirred for an hour at room temperature, then quenched by a saturated aqueous NH4Cl solution, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of ethyl acetate and n-hexane (1:10) to give ethyl N-(tert-butoxycarbonyl)-3-(4-pentenylamino)propionate (487 gm, 1.71 mmol, 46.6%) as a colourless oil.

1. additionwas added
2. washThe organic layer was washed with water and brine
3. dry with materialdried over Na2SO4
4. customevaporated in vacuo
5. dissolutionThe residue was dissolved in THF (10 mL)
6. additionwas added to the solution at 0° C
7. stirringThe mixture was stirred for an hour at room temperature
8. customquenched by a saturated aqueous NH4Cl solution
9. extractionextracted with ethyl acetate
10. washThe organic layer was washed with water and brine
11. dry with materialdried over Na2SO4
12. customevaporated in vacuo
13. customThe residue was purified by a silica gel column chromatography
14. washeluting with a mixture of ethyl acetate and n-hexane (1:10)

ORD record

ord-efdfaf7168ee4754823cf73c2e6d2aad

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06812235B2