(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.
(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.[1] and sulfite to reduce the peroxide to the acid.
Usesedit
(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.[2]
Referencesedit
^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. (4): 508–510. doi:10.1039/b713966g. ISSN 1359-7345. PMID 18188484.
^"W O 2016/119574 A 1" (PDF). Patentimages.storage.googleapis.com. Retrieved 15 March 2022.
April 13, 2024
methylpent, enoic, acid, organic, acid, with, chemical, formula, c6h10o2, other, names, this, molecule, include, methyl, pentenoic, acid, methyl, pentenoic, acid, methylallylacetic, acid, namespreferred, iupac, name, identifierscas, number, 63527, model, jsmol. 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 2R 2 Methylpent 4 enoic acid NamesPreferred IUPAC name 2R 2 Methylpent 4 enoic acidIdentifiersCAS Number 63527 49 1 Y3D model JSmol Interactive imageChemSpider 5506024EC Number 216 404 7PubChem CID 7167861UNII 4EC6RYQ4M5 YCompTox Dashboard EPA DTXSID10428231InChI InChI 1S C6H10O2 c1 3 4 5 2 6 7 8 h3 5H 1 4H2 2H3 H 7 8 t5 m1 s1Key HVRZYSHVZOELOH RXMQYKEDSA NSMILES CC CC C C O OPropertiesChemical formula C 6H 10O 2Molar mass 114 144 g mol 1Density 0 946 g cm3Melting point 87 88 C 189 190 F 360 361 K Vapor pressure 0 237 TorrAcidity pKa 4 67Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSynthesis edit 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 1 and sulfite to reduce the peroxide to the acid Uses edit 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 2 References edit 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 4 508 510 doi 10 1039 b713966g ISSN 1359 7345 PMID 18188484 W O 2016 119574 A 1 PDF Patentimages storage googleapis com Retrieved 15 March 2022 Retrieved from https en wikipedia org w index php title 2R 2 Methylpent 4 enoic acid amp oldid 1094335052, wikipedia, wiki, book, books, library,
