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

(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
Names
Preferred IUPAC name
(2R)-2-Methylpent-4-enoic acid
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 216-404-7
UNII
  • InChI=1S/C6H10O2/c1-3-4-5(2)6(7)8/h3,5H,1,4H2,2H3,(H,7,8)/t5-/m1/s1
    Key: HVRZYSHVZOELOH-RXMQYKEDSA-N
  • CC(CC=C)C(=O)O
Properties
C6H10O2
Molar mass 114.144 g·mol−1
Density 0.946 g/cm3
Melting point 87–88 °C (189–190 °F; 360–361 K)
Vapor pressure 0.237 Torr
Acidity (pKa) 4.67
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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:

  1. acylation of the oxazolidinone using triethylamine as a base, and DMAP as an acyl carrier catalyst
  2. addition of a pentene group via enolate addition using Sodium bis(trimethylsilyl)amide as a base and allyl iodide as the pentene donor
  3. and cleavage of the oxazolidinone by LiOH solution in hydrogen peroxide.[1] 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.[2]

References
  1. 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.
  2. "W O 2016/119574 A 1" (PDF). Patentimages.storage.googleapis.com. Retrieved 15 March 2022.
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