N-ACETYL-3-(NITROSOTHIO)-VALINE synthesis

Yield:273921-90-7 52%

Reaction Conditions:

with hydrogenchloride;sulfuric acid;sodium nitrite in methanol;water at 20; for 0.466667 h;

Steps:

3.3b

Pulverized L-valine, N-acetyl-3-mercapto- (484 mg, 2.53 mmol) was suspended in methanol (5 mL). IM HCl (5 mL) and sulfuric acid (0.5 mL) were added and the reaction mixture allowed to approximately room temperature. Sodium nitrite (348.4 mg, 5.05 mmol) in water (5 mL) was added dropwisely over 3 minutes. L-valine, N-acetyl-3-mercapto- dissolved and formed a green solid. The suspension was stirred at room temperature for 25 minutes. The crystals were collected by filtration, washed with water, and dried under vacuum to give the title compound (290 g, 52 % yield). ¹H NMR (300 MHz, CD₃OD) δ 5.32 (s, 1 H), 2.04 (s, 3 H), 2.01 (s, 3 H), 1.97 (s, 3 H). . LRMS (APEVIS) m/z 221 (MH⁺), 238 (MNH₄⁺).

References:

WO2007/86884,2007,A2 Location in patent:Page/Page column 75