Monomethyl succinate

It is also interesting that the yield of monomethyl succinate (R — H), which presumably arises from the abstraction of a hydrogen atom by the aeyloxy radical, is higher in the presence of aromatic than aliphatic substrates. This may mean that the aeyloxy radical is mainly responsible for the abstraction of a hydrogen atom from the initial adduct (26) formed between the alkyl radical and the aromatic substrate (cf. Section II,B). 

The synthesis of ketomethylene pseudopeptide analogues was accomplished by L. Cheng et al., and their biological activity as thrombin inhibitors was tested. These analogues were prepared through a modified Dakin-West reaction under mild conditions and in almost quantitative yield. The required anhydride was prepared from monomethyl succinate, and a large excess of it was mixed with the tripeptide substrate in pyridine in addition to triethylamine and catalytic amounts of DMAP. The reaction mixture was heated for one hour at 40-50 °C. 

Methyl hydrogen succinate Monomethyl succinate CsHsO, 3878-66-6 132.116 68 161 122< SHgO... 

Monomethyl succinate 7365 N- 1 -Naphthyl)ethylenediamine 7986 o-Nitrophenylacetic acid 8048... 

Formylacrylic acid, KGN, and NaHG03 in methanol refluxed 1 hr. with stirring monomethyl succinate. Y 90%. — Reaction in water gives succinic acid. V. Franzen and L. Fikentscher, A. 623, 68 (1959). 

Figure 6-18 shows a bell-shaped pH-rate profile for the hydrolysis of monomethyl dihydrogen phosphate. Other examples are the hydrolysis of o-carboxyphenyl hydrogen succinate and the hydration of fumaric acid. ... 

L-dihydroxy-succinic acid (L(dexiro)-tartaric acid, CXIII). This result establishes the position of the double bond between C4 and C5 and demonstrates that C4 carries only one hydrogen atom while C5 has attached to it the enolic hydroxyl group. Treatment of the enol CXI with ethereal diazomethane gives 5-methyl-A4-D-glucosaccharo-3,6-lactone methyl ester (CXIY) which upon further methylation with silver oxide and methyl iodide yields 2,5-dimethyl-A4-D-glucosaccharo-3,6-lactone methyl ester (CXV). When the latter is subjected to ozonolysis there is formed oxalic acid and 3-methyl-L-threuronic acid (CXVI). Oxidation of this aldehydic acid (CXYI) with bromine gives rise to a monomethyl derivative (CXVII) of L-ilireo-dihydroxy-succinic acid. 

Starting from the commercially available aldehyde (12), styrene (13) was prepared by a straightforward synthetic sequence (Scheme 11.3). Subsequent esterification of the phenol with succinate-derivatized poly(ethylene glycol) monomethyl ether (MeO-PEG) appended the styrene unit to approximately 50% of the free acid groups in (14). The loading in (15) was estimated by 500 MHz NMR spectroscopy to be about 0.1 mmol g . In a final step, the polymer-bound catalyst was ob-... 

Asparaginase, reaction product with succinic anhydride, esters with polyethylene glycol, monomethyl ether [CAS] Monomethoxypolyethylene glycol succinimidyl L-asparaginase [CAS]... 

In some instances the solvents may react with the substrate during the irradiation. For example, 3,6-dichloropyridazine, when irradiated in acidified methanol, gives a mixture of monomethylated (56), dimethylated (57) and hydroxymethylated (58) compounds. Further transformation of the hydroxymethyl compound (58) results in the formation of y-lactones (59) and succinates (60 Scheme 20). 

Figure 15.12. XH NMR spectra of aqueous soluble species from (A) coarse air particles with diameters of 33-4.7mm (pH 6.55) (B) fine air particles with diameters of 0.65-1.1 mm (pH 3.92). Compounds identified in the spectra include 1, acetic acid 2, monomethylamine 3, succinic acid 4, dimethylamine 5, methanesulfonic acid 6, methanol 7, monomethyl hydrogen sulfate 8, hydroxymethanesulfonic acid 9, phthalic acid 10, terephthalic acid. Reprinted from Suzuki, Y., Kawakami, M., and Akasaka, K. (2001). JH NMR application for characterizing water-soluble organic compounds in urban atmospheric particles. Environ. Sci. Technol. 35, 2656-2664, with permission from the American Chemical Society.

Another regioselective synthesis of islandicin monomethyl ether is a variation of the succinic acid synthesis (equation I). ... 

The asymmetric total synthesis of (+)-codeine, the unnatural enantiomer, was accomplished by J.D. White and coworkers using an intramolecular carbenoid insertion as the key step. The first stereogenic center that directed all subsequent stereochemical events was installed by the asymmetric hydrogenation of an alkylidene succinate that was obtained using the Stobbe condensation. Dimethyl succinate and isovanillin were reacted in the presence of excess sodium methoxide at reflux and the resulting reaction mixture was acidified to obtain the monomethyl ester. 

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