Hydroxyamine hydrochloride → Methyl 2-cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate

Into a flask containing a solution of methyl 2-formyl-1-((2-(trimethylsilyl)-ethoxy)-methyl)-1H-imidazole-4-carboxylate (9 g, 31.6 mmol) in MeOH (200 ml), 50% aqueous NH2OH.HCl solution (2.5 ml) was added and stirred at RT for 3 h. The reaction mixture was concentrated and extracted with EtOAc. The organic layer was concentrated and the resulting residue was dissolved in DCM (200 ml). Pyridine (12 ml) and trifluoroacetic anhydride (18 ml) were added to the above mixture and stirred for 12 h. The reaction mixture was quenched with aqueous NaHCO3 solution and extracted with DCM. The organic layer was concentrated and purified with flash chromatography. Yield 4.1 g. 1H-NMR (400 MHz; DMSO-d6): δ −0.04 (s, 9H), 0.87 (t, 2H), 3.56 (t, 2H), 3.81 (s, 3H), 5.29 (s, 2H), 8.28 (s, 1H).

1. additionwas added
2. concentrationThe reaction mixture was concentrated
3. extractionextracted with EtOAc
4. concentrationThe organic layer was concentrated
5. dissolutionthe resulting residue was dissolved in DCM (200 ml)
6. additionPyridine (12 ml) and trifluoroacetic anhydride (18 ml) were added to the above mixture
7. stirringstirred for 12 h
8. customThe reaction mixture was quenched with aqueous NaHCO3 solution
9. extractionextracted with DCM
10. concentrationThe organic layer was concentrated
11. custompurified with flash chromatography

ORD record

ord-6ab4675f18cb4f328b85bc5909cfb197

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921378B2