PyAOP reagent

Names
IUPAC name

(7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

Other names

PyAOP

Identifiers

CAS Number

* 156311-83-0

3D model (JSmol)

* Interactive image

ChemSpider |

* 9213814 Y

PubChem CID

* 11038641

UNII |

* C5Z532MU8E Y

InChI

* InChI=1S/C17H27N7OP.F6P/c1-2-11-21(10-1)26(22-12-3-4-13-22,23-14-5-6-15-23)25-24-17-16(19-20-24)8-7-9-18-17;1-7(2,3,4,5)6/h7-9H,1-6,10-15H2;/q+1;-1

Key: CBZAHNDHLWAZQC-UHFFFAOYSA-N

SMILES

* C1CCN(C1)[P+](N2CCCC2)(N3CCCC3)ON4C5=C(C=CC=N5)N=N4.F[P-](F)(F)(F)(F)F

Properties

Chemical formula

| C17H27F6N7OP2
Molar mass | 521.389 g·mol−1
Appearance  | White crystals
Melting point |  163–168 °C (325–334 °F; 436–441 K)
Hazards
Main hazards | Irritant

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

PyAOP ((7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate) is a reagent used to prepare amides from carboxylic acids and amines in the context of peptide synthesis.[1] It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions.[2] It is a derivative of the HOAt family of amide bond forming reagents. It is preferred over HATU, because it does not engage in side reactions with the N-terminus of the peptide.[3] Compared to the HOBt-containing analog PyBOP, PyAOP is more reactive due to the additional nitrogen in the fused pyridine ring of the HOAt moiety.[4] Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyAOP is potentially explosive.[5]

## See also

* BOP reagent

## References

1. ↑ Mansour, Tarek S.; Bardhan, Sujata; Wan, Zhao-Kui (2010). "Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications" (in en). Synlett 2010 (8): 1143–1169. doi:10.1055/s-0029-1219820. ISSN 0936-5214. http://www.thieme-connect.de/DOI/DOI?10.1055/s-0029-1219820.
2. ↑ Hoffmann, Frank; Jäger, Lothar; Griehl, Carola (2003-02-01). "Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation" (in en). Phosphorus, Sulfur, and Silicon and the Related Elements 178 (2): 299–309. doi:10.1080/10426500307942. ISSN 1042-6507. https://www.tandfonline.com/doi/full/10.1080/10426500307942.
3. ↑ Albericio, F.; Cases, M.; Alsina, J.; Triolo, S. A.; Carpino, L. A; Kates, S. (1997). "On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis". Tetrahedron Letters 38 (27): 4853–4856. doi:10.1016/S0040-4039(97)01011-3.
4. ↑ Albericio, Fernando; Bofill, Josep M.; El-Faham, Ayman; Kates, Steven A. (1998). "Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1". The Journal of Organic Chemistry (American Chemical Society) 63 (26): 9678–9683. doi:10.1021/jo980807y. ISSN 0022-3263.
5. ↑ Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F. et al. (2018-09-21). "Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing" (in en). Organic Process Research & Development 22 (9): 1262–1275. doi:10.1021/acs.oprd.8b00193. ISSN 1083-6160. https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193.

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*[CID]: Compound ID