Acetic acid, chloro(hydroxyiMino)-, 1,1-diMethylethyl ester synthesis

Yield:199169-85-2 49%

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water at 0; for 0.166667 h;

Steps:

21

[354] Preparation 21; [355] tert-Butyl 2-chloro-2-(hydroxyimino)acetate; [356] Glycine t-butyl ester HCl salt (12.Og, 71.6mmmol) synthesized according to a method known in /. of Chemical Society, PT 1, 1997, 3005 was dissolved in water (60 D ), c-HCl solution (5.97 D , l.Oeq) was added thereto once at 0⁰C, and immediately NaNO solution (4.95g in 15 D water, l.Oeq) was added thereto. Again, each l.Oeq of c- HCl and NaNO 2 solutions was added thereto. The mixture was stirred for about 10 minutes at 0⁰C, extracted with ethyl acetate (50 D x 3), washed with aqueous sodium chloride solution, dried (anhydrous Na SO ), and concentrated under reduced pressure2 4 to give the title compound (6.3g, 49%). [357]

References:

WO2006/33551,2006,A1 Location in patent:Page/Page column 27