Tetrahydro-2-furoic acid

Tetrahydro-2-furoic acid is an organic compound with the formula HO2CC4H7O. It is a colorless oil. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate relevant to the production of several drugs, including Terazosin for the treatment of prostate enlargement and hypertension.[1][2] or high boiling liquid,[3]

Tetrahydro-2-furoic acid
Names
Preferred IUPAC name
Oxolane-2-carboxylic acid
Other names
Tetrahydro-2-furoic acid; Tetrahydrofuran-2-carboxylic acid; Tetrahydrofuroic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.122.132
EC Number
  • 605-530-1
MeSH C063698
UNII
  • InChI=1S/C5H8O3/c6-5(7)4-2-1-3-8-4/h4H,1-3H2,(H,6,7)
    Key: UJJLJRQIPMGXEZ-UHFFFAOYSA-N
  • C1CC(OC1)C(=O)O
Properties
C5H8O3
Molar mass 116.116 g·mol−1
Appearance colorless oil
Density 1.262 g/cm3 @ 20 °C
Melting point 21 °C (70 °F; 294 K)
Boiling point 135 °C (275 °F; 408 K) 20 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis

Furoic acid is reduced to tetrahydro-2-furoic acid, as originally reported in 1913 by Wienhaus.[4] Tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina.[5]

Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid proceeds in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess.[6] Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid proceeds quantitatively with 24-27% enantiomeric excess in methanol solution employing a chiral, ferrocene-phosphine catalyst.[7]

Applications

Pharmaceuticals

Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile provided alfuzosin, a drug for the treatment of benign prostatic hyperplasia (BPH).[8]

A key intermediate to faropenem, an antibiotic for the treatment of acute bacterial sinusitis, chronic bronchitis and pneumonia has been prepared from tetrahydro-2-furoic acid via a process including chiral resolution and chlorination.[9]

Tecadenoson is another example of a drug made using tetrahydro-2-furoic acid.

References
  1. Wen-Chih Chou, Ming-Chen Chou, Yann-Yu Lu and Shyh-Fong Chen, "Preparation of N-acylalkylenediamines as precursors of antihypertensive quinazolines", US Patent (2001), 6313293(B1).
  2. Franco Codignola and Mario Piacenza, "A process for the production of polyurethane resins", Italian Patent (1947), ES179144 (A1).
  3. Raymond Paul; Tchelitcheff, Serge (1952). "Action of oragno-sodium derivatives on vinyl ethers". Compt. Rend. 235: 1226–8.
  4. Heinrich Wienhaus; Sorge, Hermann (1913). "Reduction of Pyromucic Acid". Berichte der Deutschen Chemischen Gesellschaft. 46: 1927–31. doi:10.1002/cber.191304602107.
  5. Zhe-qi Li; Ding, Yun-jie; Jiang, Wen-feng (2005). "Study on the performance of α-furanoic acid hydrogenation over Pd-Ni/Al2O3 catalysts under mild conditions". Fenzi Cuihua. 19 (2): 131–135.
  6. Mihaela Maris; Huck, Wolf-Rudiger; Mallat, Tamas; Baiker, Alfons (2003). "Palladium-catalyzed asymmetric hydrogenation of furan carboxylic acids". Journal of Catalysis. 219 (1): 52–58. doi:10.1016/s0021-9517(03)00184-2.
  7. Martin Studer; Wedemeyer-Exl, Christina; Spindler, Felix; Blaser, Hans-Ulrich (2000). "Enantioselective homogeneous hydrogenation of monosubstituted pyridines and furans". Monatshefte für Chemie. 131 (12): 1335–1343. doi:10.1007/s007060070013.
  8. Uday Rajaram Bapat , Jose Paul Potams, Narasimhan Subramanian and Jon Valgeirsson, "Process for the preparation of alfuzosin and salts thereof ", PCT Int. Appl. (2008), 2008152514.
  9. Hongna Han; Jin, Jie; Liu, Jun (2001). "Synthesis of key intermediate of faropenem: (3S,4R)-3-[1- ethyl]-4-(tetrahydrofuran-2- carbonylmercapto)-2-azetidinone". Shenyang Yaoke Daxue Xuebao. 18 (1): 20–22.
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