Potassium Carbonate → HCID 15035263, compound

A mixture of 1.02 g (5.85 mmol) of 9-hydroxynonanoic acid (IV4), 1 ml of thionyl chloride, and a drop portion of pyridine was heated for 3 hours on a warm bath at 70° C. and the remainder thionyl chloride was evaporated under reduced pressure. A solution of the resulting residue in 20 ml of dichloromethane was treated with 20 ml of an aqueous solution of 530 mg (6.35 mmol) of methylhydroxylamine hydrochloride and 900 mg (6.5 mmol) of potassium carbonate according to the procedure shown in Example 10 to give N-methyl-9-chlorononanohydroxamic acid (V8), which was chromatographed on silica gel eluted with ether to give 534 mg of the pure compound (V8) as a pale yellow oil in 41.1% yield. A solution of 534 g (2.4 mmol) of the compound (V8) and 580 mg (2.4 mmol) of 2,6-di-tert-butyl-4-mercaptophenol in 10 ml of ethanol was treated in the presence of 414 mg (3 mmol) of potassium carbonate and 20 mg of N-tetra-n-butylammonium iodide according to the procedure shown in Example 9. The product was chromatographed on silica gel and eluted with a mixture of dichloromethane-ethyl acetate (1:1) to give 260 mg of the aimed compound (I12) as a pale yellow oil in 25.5% yield.

1. customthe remainder thionyl chloride was evaporated under reduced pressure

ORD record

ord-483ea32e3c3246268841fda5b78b3d08

Source dataset

uspto-grants-1992_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05091569