Oxaceprol

Base Information

• Chemical Name: Oxaceprol
• CAS No.: 33996-33-7
• Molecular Formula: C7H11NO4
• Molecular Weight: 173.169
• Hs Code.: 29339900
• European Community (EC) Number: 251-780-6
• UNII: Q0XV76B96L
• DSSTox Substance ID: DTXSID2046410
• Nikkaji Number: J17.729F
• Wikipedia: Oxaceprol
• Wikidata: Q408948
• NCI Thesaurus Code: C90905
• RXCUI: 28068
• Metabolomics Workbench ID: 154180
• ChEMBL ID: CHEMBL1407356
• Mol file: 33996-33-7.mol

Synonyms:Jonctum;N-acetyl cis-4-hydroxy-L-proline;N-acetyl-4-hydroxyproline;N-acetylhydroxyproline;oxaceprol;oxaceprol, (cis)-isomer;Tejuntivo

Chemical Property of Oxaceprol

Chemical Property:

• Appearance/Colour: White fine crystals
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 132-133 °C (dec.)(lit.)
• Refractive Index: 1.4490 (estimate)
• Boiling Point: 442.1 °C at 760 mmHg
• PKA: 3.48±0.40(Predicted)
• Flash Point: 221.2 °C
• PSA: 77.84000
• Density: 1.439 g/cm³
• LogP: -1.00940
• Storage Temp.: Store at RT.
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 173.06880783
• Heavy Atom Count: 12
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

Acetyl-L-4-hydroxyproline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)N1CC(CC1C(=O)O)O
• Isomeric SMILES: CC(=O)N1C[C@@H](C[C@H]1C(=O)O)O
• Uses: trans-1-Acetyl-4-hydroxy-L-proline can be used:In the stereospecific synthesis of 4-fluoroglutamic acid.To synthesize molecular targets for von Hippel-Lindau (VHL) E3 ubiquitin ligase.As a precursor to synthesize pseudopoly(amino acids) such as poly(trans-4-hydroxy-4-acyl-L-proline ester) and a biodegradable polymer, poly(lactic acid-glycolic acid-4-hydroxyproline).
• Therapeutic Function: Antirheumatic

Technology Process of Oxaceprol

There total 13 articles about Oxaceprol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 70.0%

acetic anhydride (108-24-7) + 4R-4-hydroxyproline (51-35-4,30724-02-8) → oxaceprol (33996-33-7)

Guidance literature:

In water; at 40 - 50 ℃; for 3h;

Reference yield:

(2S,4R)-N-acetyl-4-benzoyloxy-proline (43176-83-6) → oxaceprol (33996-33-7)

Guidance literature:

With sodium hydroxide;

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → oxaceprol (33996-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aqueous NaOH / 0 °C / anschliessend Behandeln mit Benzoylchlorid

2: aqueous NaOH

With sodium hydroxide;

upstream raw materials:

(2S,4R)-N-acetyl-4-benzoyloxy-proline

acetic anhydride

4R-4-hydroxyproline

cis-4-hydroxyproline

Downstream raw materials:

(2S,4R)-1-acetyl-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

N-[(3S,4R)-1-((2S,4R)-1-acetyl-4-hydroxy-pyrrolidine-2-carbonyl)-4-phenyl-pyrrolidin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide

C₂₇H₂₉FN₄O₃

cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline-methyl ester

Refernces

• 1、 -. "Process for the preparation of teneligliptin". Page/Page column 28. . Retrieved 2017/01/02.
• 2、 -. "BIOSYNCHRONOUS TRANSDERMAL DRUG DELIVERY". . . Retrieved 2008/06/13.