4,4,5,5,5-Pentafluoro-1-pentanol (also known as pentafluoropentanol or PFP, CAS 148043-73-6) is an important building block primarily used in the commercial manufacture of the API fulvestrant. Using proprietary technology, Valliscor manufactures kilogram to commercial scale quantities of PFP for the pharmaceutical industry at its Corvallis, Oregon production facility. To find out more information about any of our offerings including pentafluoropentanol (PFP), please contact us at info@valliscor.com.
Alternate Names: PFP, pentafluoropentanol, 4,4,5,5,5-pentafluoropentan-1-ol, 4,4,5,5,5-pentafluoropentanol
Catalog #: VCPFP
CAS #: 148043-73-6
Molecular Weight: 178.10
Boiling Point: 133°C
Density: 1.35 g/mL
PubChem Link Page: https://pubchem.ncbi.nlm.nih.gov/compound/4_4_5_5_5-Pentafluoropentan-1-ol
Material Safety Data Sheet (MSDS) / Safety Data Sheet (SDS): [DOWNLOAD]
4,4,5,5,5-Pentafluoro-1-pentanol (PFP, CAS 148043-73-6) is an important building block primarily used in the commercial manufacture of the API fulvestrant. First approved by the FDA in 2002, fulvestrant is a medication used to treat hormone receptor (HR)-positive metastatic breast cancer in postmenopausal women with disease progression. This API was originally developed by AstraZeneca under the trade name Faslodex©. In 2016, fulvestrant was approved by the FDA in combination with palbociclib to treat HR-positive, HER2-negative advanced breast cancer in women with disease progression after endocrine therapy.
4,4,5,5,5-pentafluoro-1-pentanol (PFP, CAS 148043-73-6) is typically activated with a sulfonate leaving group and displaced selectively by the sulfur atom in 9-mercapto-1-nonanol to make 9-[(4,4,5,5,5-pentafluoropentyl)-thio]-1-nonanol (FVS, CAS # 511545-94-1). FVS is subsequently converted into a bromide and coupled with the steroid portion to make fulvestrant.
Valliscor also manufactures FVS for customers looking for a more advanced intermediate.
For more information, see: (a) Org. Proc. Res. Dev. 2010, 14 (3), 544-552
. (b) U.S. Patent WO2006015081, February 9, 2006. (c) U.S. Patent WO2014064712, May 1, 2014. (d) Chem. Commun. 2015, 51 (80), 14866-14868
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French researchers reported the synthesis of RU-58,668 - a steriodal antiestrogen that displayed potent antiproliferative activity on the MCF-7 human mammary cancer cell line (Eq. 4, see J. Steriod Biochem. Molec. Biol.1994, 48, 187-196). 4,4,5,5,5-pentafluoro-1-pentanol (PFP, CAS 148043-73-6) was converted with triphenyl phosphine, iodine and imidazole to the corresponding iodide (PFIP). PFIP was in turn coupled with the in situ generated thiol followed by oxidation to the sulfone to provide RU-58,668.
Patients with estrogen receptor α (ERα)-positive breast cancer can experience the recurrence of drug- resistant metastases after initial successful treatment with endocrine therapies (ACS Chem. Biol.2018, 13, 3374−3384). Sharma and co-workers have synthesized a series of C2F5 containing drug candidates that have shown encouraging early success at addressing this issue. They employ a similar strategy as others for the incorporation the side arm using 4,4,5,5,5-pentafluoro-1-pentanol (PFP, CAS 148043-73-6) (Eq. 5).
