Dexpemedolac

Base Information

• Chemical Name: Dexpemedolac
• CAS No.: 114030-44-3
• Molecular Formula: C22H23 N O3
• Molecular Weight: 349.42
• UNII: P7VK7RH5C7,5285077I2I
• Nikkaji Number: J404.471A
• Wikidata: Q106641398
• NCI Thesaurus Code: C166805,C174836
• ChEMBL ID: CHEMBL430916
• Mol file: 114030-44-3.mol

Synonyms:1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano(3,4-b)indole-1-acetic acid;pemedolac

Chemical Property of Dexpemedolac

Chemical Property:

• Vapor Pressure: 7.25E-15mmHg at 25°C
• Melting Point: 170-171.5 °C(Solv: isopropanol (67-63-0))
• Boiling Point: 592.1°Cat760mmHg
• PKA: 4.31±0.10(Predicted)
• Flash Point: 311.9°C
• PSA: 62.32000
• Density: 1.22g/cm³
• LogP: 4.60440
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 349.16779360
• Heavy Atom Count: 26
• Complexity: 504

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(C(CO1)CC3=CC=CC=C3)C4=CC=CC=C4N2)CC(=O)O
• Isomeric SMILES: CC[C@@]1(C2=C([C@H](CO1)CC3=CC=CC=C3)C4=CC=CC=C4N2)CC(=O)O
• Uses: Analgesic.

Technology Process of Dexpemedolac

There total 21 articles about Dexpemedolac 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:

ethyl 2-(1H-indol-3-yl)-2-oxoacetate (51079-10-8) → (1S,4R)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-B]indole-1-acetic acid (114030-44-3,114716-16-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 95 percent / NaOAc, NH₂OH*HCl / ethanol; H₂O / 1.) reflux, 5 h, 2.) room temperature, overnoght

2: 80 percent / HCl, H₂ / 5percent Pd/C / ethanol / 4 h / 2068.6 Torr / Ambient temperature

3: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

4: 94 percent / 18 h / Ambient temperature

5: 98 percent / 5percent K₂CO₃ / methanol / 2 h / Heating

6: 64 percent / BF₃*Et₂O / CH₂Cl₂ / 16 h

7: 97 percent / 1N HCl / methanol / 24 h / 25 °C

8: 66 percent / H₂O, paraformaldehyde / tetrahydrofuran / 2 h / Heating

9: TiCl₄ / CH₂Cl₂; diethyl ether / 0.5 h / -78 °C

10: 10percent aq. NaOH / ethanol / 2 h / Heating

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; formaldehyd; boron trifluoride diethyl etherate; hydroxylamine hydrochloride; water; hydrogen; sodium acetate; titanium tetrachloride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;

DOI:10.1021/jm00401a029

Reference yield:

ethyl 3-indoleglyoxylate oxime (91393-10-1) → (1S,4R)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-B]indole-1-acetic acid (114030-44-3,114716-16-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / HCl, H₂ / 5percent Pd/C / ethanol / 4 h / 2068.6 Torr / Ambient temperature

2: 90 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

3: 94 percent / 18 h / Ambient temperature

4: 98 percent / 5percent K₂CO₃ / methanol / 2 h / Heating

5: 64 percent / BF₃*Et₂O / CH₂Cl₂ / 16 h

6: 97 percent / 1N HCl / methanol / 24 h / 25 °C

7: 66 percent / H₂O, paraformaldehyde / tetrahydrofuran / 2 h / Heating

8: TiCl₄ / CH₂Cl₂; diethyl ether / 0.5 h / -78 °C

9: 10percent aq. NaOH / ethanol / 2 h / Heating

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; formaldehyd; boron trifluoride diethyl etherate; water; hydrogen; titanium tetrachloride; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/jm00401a029

Reference yield:

benzyl chloride (100-44-7) → (1S,4R)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-B]indole-1-acetic acid (114030-44-3,114716-16-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / LDA / tetrahydrofuran; cyclohexane / 1.) -5 deg C, 2 h, 2.) room temperature, 18 h

2: 97 percent / H₂SO₄ / 2 h / Heating

3: 92 percent / NaBH₄, CH₃OH / tetrahydrofuran / 60 - 70 °C

4: BF₃*Et₂O / toluene / -15 °C

5: 10percent aq. NaOH / ethanol / 2 h / Heating

With methanol; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; boron trifluoride diethyl etherate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; cyclohexane; toluene;

DOI:10.1021/jm00401a029

upstream raw materials:

cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano<3,4-b>indole-1-acetic acid methyl ester

indole-3-acetic acid

Indole-3-acetic acid methyl ester

(E)-methyl 3-methoxypent-2-enoate

Refernces

• 1、 Katz, Alan H.,Demerson, Christopher A.,Shaw, Chia-Cheng,Asselin, Andre A.,Humber, Leslie G.,et al.. "Synthesis and Analgesic Activity of Pemedolac (cis-1-Ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyranoindole-1-acetic Acid)". . p. 1244 - 1250. Retrieved 2007/10/02.