Methanol → HCID 14860720, compound

An aqueous solution (20 mL) of NaIO4 (3.00 g, 14.02 mmol) was added to a MeOH solution (20 mL) of 2-acetamido-N-benzyl-2-(ethylmercapto)acetamide (0.95 g, 3.57 mmol). The initial homogeneous solution rapidly became turbid. H2O (~10 mL) was then added dropwise until the system became homogeneous. The solution was stirred (18 h) at 50°-60° C. MeOH (50 mL) was added to the reaction solution and the precipitated salt was filtered and washed with MeOH (10 mL). The filtrate was concentrated and the remaining solution was extracted with CHCl3 (3×50 mL). The combined CHCl3 extracts were dried (Na2SO4), and concentrated in vacuo. The residue was purified by flash chromatography on SiO2 gel (1% MeOH/CHCl3) to give the desired product. The product was further purified by recrystallization from EtOH:.

1. filtrationthe precipitated salt was filtered
2. washwashed with MeOH (10 mL)
3. concentrationThe filtrate was concentrated
4. extractionthe remaining solution was extracted with CHCl3 (3×50 mL)
5. dry with materialThe combined CHCl3 extracts were dried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customThe residue was purified by flash chromatography on SiO2 gel (1% MeOH/CHCl3)

ORD record

ord-b293335825ac4f26ac7e52606056137a

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05378729