naproxen glucuronide

Base Information

• Chemical Name: naproxen glucuronide
• CAS No.: 41945-43-1
• Molecular Formula: C20H22O9
• Molecular Weight: 406.389
• Hs Code.: 2932990090
• Mol file: 41945-43-1.mol

Synonyms:Naproxen Acyl--D-glucuronide;(S)-Naproxen Glucuronide;(S)-Naproxen Acyl-Beta-D-glucuronide;(+)-Naproxen glucuronide;1-[(aS)-6-Methoxy-a-methyl-2-naphthaleneacetate]-D-Glucopyranuronic Acid;

Chemical Property of naproxen glucuronide

Chemical Property:

• Vapor Pressure: 2.2E-17mmHg at 25°C
• Melting Point: 80-82oC
• Boiling Point: 642.5°Cat760mmHg
• PKA: 2.67±0.70(Predicted)
• Flash Point: 227.6°C
• PSA: 142.75000
• Density: 1.48g/cm³
• LogP: 0.38730
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-NaproxenAcyl-β-D-glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 8167705
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of naproxen glucuronide

There total 6 articles about naproxen glucuronide 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: 100.0%

C27H28O9 (946517-36-8) → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

With cyclohexa-1,4-diene; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol; for 2h; Heating;

DOI:10.1016/j.tet.2007.05.050

Reference yield: 99.0%

benzyl 1-O-[(S)-2-(6-methoxy-2-naphthyl)propionyl]-2,3,4-tri-O-benzyl-β-D-glucopyranuronate → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; under 760 Torr;

DOI:10.1081/CAR-120034003

Reference yield:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) → (+)-Naproxen glucuronide (41945-43-1,112828-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / HATU; N-methylmorpholine / acetonitrile / 20 °C

2: 100 percent / cyclohexa-1,4-diene / Pd-C / tetrahydrofuran; propan-2-ol / 2 h / Heating

With 4-methyl-morpholine; cyclohexa-1,4-diene; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; isopropyl alcohol; acetonitrile;

DOI:10.1016/j.tet.2007.05.050

upstream raw materials:

C₂₇H₂₈O₉

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

benzyl <1-O-trichloroethanimidoyl>-2,3,4-tri-O-benzyl-D-glucopyranuronate

(S)-naproxen 1-β-O-acyl glucuronide methyl ester

Downstream raw materials:

(2S)-2-(6-methoxy(2-naphthyl))propanoic acid

S-naproxen α-1-O-acyl glucuronide

Refernces

• 1、 Baba, Akiko,Yoshioka, Tadao. "Synthesis of 1-β-O-acyl glucuronides of diclofenac, mefenamic acid and (S)-naproxen by the chemo-selective enzymatic removal of protecting groups from the corresponding methyl acetyl derivatives". . p. 3303 - 3310. Retrieved 2008/09/17.