(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

white to light yellow to beige crystalline powder

(S)-alpha-hydroxyglutaric acid-gamma-lactone is a butan-4-olide obtained by formal intramolecular condensation between the 2-hydroxy and 4-carboxy groups of (S)-2-hydroxyglutaric acid It is a butan-4-olide and a monocarboxylic acid. It derives from a (S)-2-hydroxyglutaric acid. It is a conjugate acid of a (S)-alpha-hydroxyglutarate-gamma-lactone.

(S)-(+)-5-Oxo-2-tetrahydrofurancarboxylic acid is a chiral derivatizing agent for alcohols.

To a solution of L-glutamic acid (10.07 g, 0.068 mol, Jl-glutamic acid (30.0g, 200mmol) was suspended in a water/ dioxane mixture (75/25mL) and stirred at 0°C for 30min. The white slurry became clear after 40mL of concentrated HCl (37percent) was added, followed by drop-wise addition of a solution of NaNOTo a solution of L-glutamic acid in water, an aqueous solution of NaNOA solution of sodium nitrite (140 g, 2.03 mol) in water (320 mL) was added over 4 h to a mixture of L-glutamic acid (200 g, 1.36 mol), dioxane (150 mL) and HCl (280 mL) in water (530 mL) and maintained at an internal temperature of 0-5° C. Some evolution of nitric oxide (brown gas) was observed. HPLC monitoring indicated that the reaction was complete once the addition of a stoichiometric amount of aqueous sodium nitrite was added (e.g., after approx. 30 min. for a reagent addition step requiring 45 minutes to complete). Further investigation using an in situ ReactIR probe indicated that the reaction required 2 h reaction time after the addition of the aqueous sodium nitrite solution. On completion of the addition, the mixture was warmed to r.t. and stirred 2 h, then solvents were removed in vacuo at 50-55° C. The residue was coevaporated with toluene (2.x.500 mL) to remove additional water, then ethyl acetate (1 L) was added, followed by sodium sulfate (100 g), and the mixture was stirred 0.5 h. The ethyl acetate solution was decanted and filtered, and the solids were washed and stirred with additional ethyl acetate (1 L). The combined filtrates were concentrated in vacuo, and the resulting residue was further dried under high vacuum (1 torr). The mass of crude residue containing EP2104-01 was 184 g, exceeding the mass of the theoretical yield by 7 g, attributable to solvent trapped by the viscous, syrupy residue. A sample of this residue was subjected to chiral GC analysis, which indicated the optical purity of this material to be 93.5percent e.e.(2S-2-Arninopentanedioic acid (2.50 kg, 16.99 mol) was dissolved in H20 (6 L) andconcentrated HC1 (3.5 L), then a solution ofNaNO2 (1.76 kg, 25.49 mol) in H20 (5 L) was addedslowly at -5 °C to 0 °C. After being stirred at 28 °C for 16 hours, the reaction mixture was concentrated below 50 °C to give a residue, which was treated with EtOAc (5 L). After being filtered , the filtrate was dried over Na2SO4 and concentrated in vacuo to give 1.5 kg of(2S-5-oxotetrahydrofuran-2-carboxylic acid as a colorless oil which was used for the next step without further purification.

(S)-5-Oxo-2-tetrahydrofurancarboxylic Acid (cas# 21461-84-7) is a compound useful in organic synthesis.

Molecular Weight:130.10
XLogP3:-0.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:130.02660867
Monoisotopic Mass:130.02660867
Topological Polar Surface Area:63.6
Heavy Atom Count:9
Complexity:151
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes