(2R)-2-Methylpent-4-enoic acid

(2R)-2-Methylpent-4-enoic acid (2R)-2-Methylpent-4-enoic acid File:(R)-2-methylpent-4-enoic acid.svg 7167861 63527-49-1 correct CAS correct FDA 4EC6RYQ4M5 216-404-7 5506024 1S/C6H10O2/c1-3-4-5(2)6(7)8/h3,5H,1,4H2,2H3,(H,7,8)/t5-/m1/s1 HVRZYSHVZOELOH-RXMQYKEDSA-N CC(CC=C)C(=O)O 6 10 2 0.946 g/cm3 87-88 0.237 Torr 4.67 (2R)-2-Methylpent-4-enoic acid is an organic acid with the chemical formula C6H10O2. Other names for this molecule include (R)-2-methyl-4-pentenoic acid, (R)-(−)-2-methyl-4-pentenoic acid, and methylallylacetic acid. Synthesis (R)-2-Methylpent-4-enoic acid can be synthesized using a chiral auxiliary such an oxazolidinone derivative, popularized by David Evans. One route of synthesis consists of three steps: acylation of the oxazolidinone using triethylamine as a base, and DMAP as an acyl carrier catalyst addition of a pentene group via enolate addition using Sodium bis(trimethylsilyl)amide as a base and allyl iodide as the pentene donor and cleavage of the oxazolidinone by LiOH solution in hydrogen peroxide.Green Rachel Merritt Andrew T. Bull Steven D. 2008 A cleavable linker strategy for optimising enolate alkylation reactions of a polymer-supported Evans' oxazolidin-2-one Chem. Commun. en 4 508–510 10.1039/b713966g 18188484 1359-7345 and sulfite to reduce the peroxide to the acid. Uses (R)-2-Methylpent-4-enoic acid can also be used in synthesis of other chiral compounds. For example, it has been used in the process of synthesizing the drug Sacubitril as a reagent for adding a chiral center to the molecule.https://patentimages.storage.googleapis.com/32/a0/a5/63bfaa325a4c5a/WO2016119574A1.pdf PDF W O 2016/119574 A 1 Patentimages.storage.googleapis.com 15 March 2022 References Category:Carboxylic acids Category:Alkene derivatives