2432-99-7Relevant articles and documents
Syntheses of 12-aminododecanoic and 11-aminoundecanoic acids from vernolic acid
Ayorinde, Folahan O.,Nana, Erick Y.,Nicely, Pete D.,Woods, Anthony S.,Price, Elvis O.,Nwaonicha, Chukwuma P.
, p. 531 - 538 (1997)
12-Aminododecanoic acid and 11-aminoundecanoic acid, monomer precursors for nylon-12 and nylon-11, respectively, have been synthesized from vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid via a reaction sequence that includes the formation of 12-oxododecanoic acid oxime. Saponification of vernonia oil, followed by a low-temperature recrystallization at -20°C, gave 51% vernolic acid (97% purity, m.p. 23-25°C). Hydrogenation afforded cis-12,13-epoxystearic acid (m.p. 52-54°C, lit. m.p. 52-54°C), which upon oxidation with periodic acid in tertiary butyl alcohol gave 12-oxododecanoic acid with an isolated yield of 71.0%. Reaction of the oxoacid with hydroxylamine hydrochloride gave 12-oxododecanoic acid oxime, which was catalytically reduced to give 12-aminododecanoic acid with a yield greater than 85% and a melting point of 184-186°C (lit. m.p. 185-187C). 11-Aminoundecanoic acid was prepared from the 12-oxododecanoic acid oxime via a three-step reaction sequence that involved a Beckmann rearrangement, Hofmann degradation, and hydrolysis. Thus, the aldoxime acid was hydrolyzed in the presence of nickel acetate tetrahydrate to give 11-carbamoylundecanoic acid (48% yield, m.p. 129-131°C, lit. m.p. 129-130°C). The amide was then treated with a solution of sodium methoxide and bromine at 70-80°C to give 11-(methoxycarbonylamino)undecanoic acid at 75% yield (m.p. 84-86°C; elemental analysis, calculated for C13H25NO4: C, 60.19; H, 9.73; N, 5.40; O, 24.68%; found C, 60.02; H, 9.81; N, 5.26; O, 24.91%), which upon alkaline hydrolysis and subsequent neutralization gave 11-aminoundecanoic acid at 34% yield (m.p. 189-192°C, lit. m.p. 190°C). Mass spectrometric and 13C nuclear magnetic resonance data of the previously unreported 11-(methoxycarbonylamino)undecanoic acid is provided.
CONJUGATED CHEMICAL INDUCERS OF DEGRADATION AND METHODS OF USE
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Page/Page column 438, (2020/05/28)
The subject matter described herein is directed to antibody-CIDE conjugates (Ab-CIDEs), to pharmaceutical compositions containing them, and to their use in treating diseases and conditions where targeted protein degradation is beneficial.
Method of Preparing Aminoundecane Acid and 11-Aminoundecanoic Acid or Structural Isomer Thereof by Hydroformylation Reaction
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Paragraph 0112-0116; 0119-0136, (2020/11/03)
The present invention relates to a method for preparing 11-aminoundecanoic acid or structural isomers thereof using a hydroformylation reaction. More particularly, the present invention is an eco-friendly method capable of preparing aminoundecanoic acid used as a monomer of polyamide and structural isomers thereof from an olefinic acid ester obtained through a metathesis reaction of oleic acid by means of hydroformylation, reductive amination reaction, and hydrolysis reaction, and capable of producing various polyamides having different physical properties according to a ratio of each isomer since the ratio of structural isomers can be adjusted according to a ligand.COPYRIGHT KIPO 2021