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

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

(R)-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:

  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 chircal center to the molecule[2].

Properties

Physical Properties
Molecular Weight 114.14 g/mol
Boiling Point 87-88 °C[3]
Density 0.946 g/cm3
pKa 4.67
Optically Active Yes
Vapor Pressure 0.237 Torr

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. 0 (4): 508–510. doi:10.1039/b713966g. ISSN 1359-7345.
  2. ^ https://patentimages.storage.googleapis.com/32/a0/a5/63bfaa325a4c5a/WO2016119574A1.pdf
  3. ^ Stallberg, Gunnel (1957). "Preparation of the levorotatory enantiomer of methylallylacetic acid". Acta Chemica Scandinavica. 11: 1430.


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