PyAOP reagent

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| ImageFile = PyAOP Structure.svg

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| IUPACName = (7-Azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate

| OtherNames = PyAOP

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9213814

| 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

| InChIKey = CBZAHNDHLWAZQC-UHFFFAOYSA-N

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| CASNo_Ref =

| CASNo = 156311-83-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = C5Z532MU8E

| PubChem = 11038641

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

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|Section2={{Chembox Properties

| C=17 | H=27 | N=7 | O=1 | P=2 | F=6

| Appearance = White crystals

| Density =

| MeltingPtC = 163-168

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|Section3={{Chembox Hazards

| MainHazards = Irritant

| FlashPt =

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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.{{Cite journal |last=Mansour |first=Tarek S. |last2=Bardhan |first2=Sujata |last3=Wan |first3=Zhao-Kui |date=2010 |title=Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications |url=http://www.thieme-connect.de/DOI/DOI?10.1055/s-0029-1219820 |journal=Synlett |language=en |volume=2010 |issue=08 |pages=1143–1169 |doi=10.1055/s-0029-1219820 |issn=0936-5214}} It can be prepared from 1-hydroxy-7-azabenzotriazole (HOAt) and a chlorophosphonium reagent under basic conditions.{{Cite journal |last=Hoffmann |first=Frank |last2=Jäger |first2=Lothar |last3=Griehl |first3=Carola |date=2003-02-01 |title=Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation |url=https://www.tandfonline.com/doi/full/10.1080/10426500307942 |journal=Phosphorus, Sulfur, and Silicon and the Related Elements |language=en |volume=178 |issue=2 |pages=299–309 |doi=10.1080/10426500307942 |issn=1042-6507}} 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.{{Cite journal | doi = 10.1016/S0040-4039(97)01011-3 | title = On the use of PyAOP, a phosphonium salt derived from HOAt, in solid-phase peptide synthesis | year = 1997 | last1 = Albericio| first1 = F. |last2 = Cases| first2 = M. | last3 = Alsina | first3 = J. | last4 = Triolo | first4 = S. A. | last5 = Carpino | first5 = L. A | last6 = Kates | first6 = S. | journal = Tetrahedron Letters | volume = 38 | issue = 27 | pages = 4853–4856}} 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.{{cite journal |title=Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1|author1=Albericio, Fernando|author2=Bofill, Josep M.|author3=El-Faham, Ayman|author4=Kates, Steven A.|year=1998|journal=The Journal of Organic Chemistry|pages=9678–9683|volume=63|issue=26|publisher=American Chemical Society|issn=0022-3263|doi=10.1021/jo980807y}} Thermal hazard analysis by differential scanning calorimetry (DSC) shows PyAOP is potentially explosive.{{Cite journal |last=Sperry |first=Jeffrey B. |last2=Minteer |first2=Christopher J. |last3=Tao |first3=JingYa |last4=Johnson |first4=Rebecca |last5=Duzguner |first5=Remzi |last6=Hawksworth |first6=Michael |last7=Oke |first7=Samantha |last8=Richardson |first8=Paul F. |last9=Barnhart |first9=Richard |last10=Bill |first10=David R. |last11=Giusto |first11=Robert A. |last12=Weaver |first12=John D. |date=2018-09-21 |title=Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing |url=https://pubs.acs.org/doi/10.1021/acs.oprd.8b00193 |journal=Organic Process Research & Development |language=en |volume=22 |issue=9 |pages=1262–1275 |doi=10.1021/acs.oprd.8b00193 |issn=1083-6160}}