(5-Carboxypentyl)(triphenyl)phosphonium bromide

Chemical Properties

White Crystalline Solid

Uses

(5-Carboxypentyl)(triphenyl)phosphonium bromide is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.
Reactant for:

1. Preparation of inhibitor of protein tyrosine phosphatase 1B for treatment of diabetes and obesity.
2. Synthesis of folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity.
3. Preparation of peptide nucleic acids (PNA) with high specific activity.
4. Synthesis of roseophilin via Wittig/aldol methodology.

Uses

It is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.

Synthesis

4224-70-8

603-35-0

50889-29-7

General procedure for the synthesis of 5-carboxypentyltriphenylphosphonium bromide from 6-bromohexanoic acid and triphenylphosphine: 6-bromohexanoic acid (10.00 g, 51.27 mmol) and triphenylphosphonium (14.12 g, 53.83 mmol) were dissolved in freshly distilled acetonitrile (50 mL) and the reaction mixture refluxed for 48 h under vigorous stirring. Upon completion of the reaction, the solution was cooled to room temperature and precipitation of Wittig salt was induced by scraping the inner wall of the glass reactor. The resulting white solid product was collected by filtration and washed with ether to give the final 5-carboxypentyltriphenylphosphonium bromide in 98% (22.87 g) yield. The structure of the product was confirmed by 1H NMR (400 MHz, CD3OD): δ 1.62-1.72 (m, 6H), 2.29 (t, 2H), 3.40-3.47 (m, 2H), 7.76-7.91 (m, 15H).

References

[1] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 321 - 330
[2] Analytical Chemistry, 2006, vol. 78, # 1, p. 71 - 81
[3] Journal of Organic Chemistry, 2004, vol. 69, # 14, p. 4615 - 4625
[4] Journal of Natural Products, 2001, vol. 64, # 11, p. 1426 - 1429
[5] Patent: WO2008/30532, 2008, A2. Location in patent: Page/Page column 41