Methyl 3-mercaptopropanoate

To a solution of isophthalaldehyde (40 g, 0.3 mol.) in chloroform (400 ml) and methyl 3-mercaptopropanoate (68 ml, 0.6 mol) was added dropwise trimethylsilyl chloride (48 ml, 0.38 mol) over 30 min. The reaction mixture was stirred at room temperature for 2 hours. The reaction was quenched with 25% aq. NH4OAc, extracted with ethyl acetate, dried and evaporated. Flash chromatography of the residue afforded 50 g of the title compound. 

Michael addition of methyl 3-mercaptopropanoate to methyl 3-methylbut-2-enoate and Dieckmann cyclization of the resulting diester yields 2,2-dimethyltetrahydrothiopyran-4-one 539 (Scheme 220) <2005HCA1922>. Similarly, diethyl thiodipropanoate, accessible from ethyl propenoate by treatment with NaSH in methanol, cyclizes to ethyl 4-oxotetrahydrothiopyran-3-carboxylate under basic conditions. The carbon skeleton has also been provided by 1,4-pentadienones <1995JOC1665> and H2S in ethanol has been used as an alternative source of the heteroatom (Scheme 221) <1999SL735>. 

Methyl magnesium bromide Methylmagneslum chloride Methylmalonic acid Methyl mercaptoacetate Methyl 3-mercaptopropanoate Methylmercuricdicyanamide... 

The treatment of 2,3,4,6-tetra-0-acetyl-2-hydroxy-D-glucal with allyl trimethylsilane or methyl-3-mercaptopropanoate under Lewis acid catalysis gave a ... 

Ortho esters were reduced to acetals. Refluxing with 0.25mol of lithium aluminum hydride in ether-benzene solution for 4 hours transformed 3-methyl-mercaptopropanoic acid trimethyl orthoester to 3-methylmercaptopropion-aldehyde dimethylacetal in 97% yield [1098]. 

Hydroxy-3-mercaptopropanoic acid)]oxytOcin hydroxyoxytocin. hydroxy-/V-methylmorphinan (3-hydroxy-/V-methylmorphinan) is one of the phenanthrene series, an OPIOID RECEPTOR AGONIST, OPIOID ANALGESIC and ANTITUSSIVE. It can be used in the (+)-form, dextrorphan (-)-form, levorphanol ( )-form, racemorphan and the methyl ester derivatives of these. 

Synthesis of 2-Benzamido-2-mercaptopropanoic Acid from 4-Methyl-2-phenyl-... 

---