Methyl hydrogen adipate is a useful synthetic intermediate. It can be used to prepare 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors which show potential antitumor activities. It can be also used to synthesize mannose-linked biphenylylacetic acid derivatives as novel inhibitors of selectin-mediated cell adhesion.
Peng Guan; Fenge Sun; Xuben Hou; Feng Wang; Fan Yi; Wenfang Xua; Hao Fang. Design, synthesis and preliminary bioactivity studies of 1,3,4-thiadiazole hydroxamic acid derivatives as novel histone deacetylase inhibitors. Bioorganic & Medicinal Chemistry,2012, 20 (12), 3865-3872.
Yoo Tanabe. The Selective Claisen and Dieckmann Ester Condensations Promoted by Dichlorobis(trifluoromethanesulfonato)titanium(IV). Bulletin of the Chemical Society of Japan, 1989, 62 (6), 1917-1924.
The formation of ketones from carboxylic acids is illustrated by the conversion of methyl hydrogen adipate to the mono-acid chloride using 1-chloro-N,N,2-trimethylpropenylamine, followed by Cu(I)-promoted reaction with butylmagnesium bromide: Chem. Lett., 1791 (1983); Org. Synth. Coll., 8, 441 (1993):