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

(2R)-2-Methylpent-4-enoic acid
Names
	Preferred IUPAC name (2R)-2-Methylpent-4-enoic acid
Identifiers
CAS Number	63527-49-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	5506024;
EC Number	216-404-7;
PubChem CID	7167861;
UNII	4EC6RYQ4M5 ;
CompTox Dashboard (EPA)	DTXSID10428231 ;
	InChI 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;
	SMILES CC(CC=C)C(=O)O;
Properties
Chemical formula	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

(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.^[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

^ 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.

[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.

[1]

[2]