(S)-Sulindac

Base Information

• Chemical Name: (S)-Sulindac
• CAS No.: 149116-77-8
• Molecular Formula: C₂₀H₁₇FO₃S
• Molecular Weight: 356.418
• UNII: P969C405OM
• Wikidata: Q26998355
• ChEMBL ID: CHEMBL3527054
• Mol file: 149116-77-8.mol

Synonyms:S-sulindac

Chemical Property of (S)-Sulindac

Chemical Property:

• Boiling Point: 581.6±50.0 °C(Predicted)
• PKA: 4.26±0.10(Predicted)
• PSA: 73.58000
• Density: 1.38±0.1 g/cm3(Predicted)
• LogP: 5.23120
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 356.08824374
• Heavy Atom Count: 25
• Complexity: 616

Purity/Quality:

98% ^*data from raw suppliers

(S)-Sulindac ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C2=C(C1=CC3=CC=C(C=C3)S(=O)C)C=CC(=C2)F)CC(=O)O
• Isomeric SMILES: CC\1=C(C2=C(/C1=C\C3=CC=C(C=C3)[S@@](=O)C)C=CC(=C2)F)CC(=O)O
• Uses: (S)-Sulindac is the S-epimer metabolite of Sulinac (S699215). (S)-Sulindac increases the activity of the P 450 system better than (R)-Sulindac, but both epimers increase primarily the enzymes that oxidize (R)-Sulindac.

Technology Process of (S)-Sulindac

There total 2 articles about (S)-Sulindac 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: 94.0%

5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid (49627-27-2,61812-45-1,32004-67-4) → 2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid (38194-50-2,49627-22-7,53933-60-1,61812-46-2,149116-77-8,32004-68-5)

Guidance literature:

With oxygen; In methanol; water; at 20 ℃; for 13h; Irradiation; Green chemistry;

DOI:10.1039/d1gc02733f

Reference yield: 87.0%

→ 2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid (38194-50-2,49627-22-7,53933-60-1,61812-46-2,149116-77-8,32004-68-5)

Guidance literature:

Reference yield: 84.0%

2-(5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)acetic acid (38194-50-2,49627-22-7,53933-60-1,61812-46-2,149116-77-8,32004-68-5) + 2,2,2,-trichloroethoxycarbonyl azide → 2,2,2-trichloroethyl ((5-fluoro-2-methyl-1-(4-(methylsulfinyl)benzylidene)-1H-inden-3-yl)methyl)carbamate

Guidance literature:

With dmap; copper diacetate; In acetonitrile; at 80 ℃; for 3h; Schlenk technique; Sealed tube;

DOI:10.1002/anie.202010974

upstream raw materials:

5-fluoro-2-methyl-1-(4-methylsulfanylbenzylidene)-3-indenylacetic acid

Downstream raw materials:

{6-Fluoro-3-[1-(4-methanesulfinyl-phenyl)-meth-(E)-ylidene]-2-methyl-3H-inden-1-yl}-methanol

6-Fluoro-3-[1-(4-methanesulfinyl-phenyl)-meth-(E)-ylidene]-2-methyl-3H-indene-1-carbaldehyde

6-Fluoro-3-[1-(4-methanesulfonyl-phenyl)-meth-(E)-ylidene]-2-methyl-3H-indene-1-carbaldehyde

{6-Fluoro-3-[1-(4-methanesulfonyl-phenyl)-meth-(E)-ylidene]-2-methyl-3H-inden-1-yl}-methanol

Refernces

• 1、 -. "Sulfoxide and sulfone compounds, as well as selective synthesis method and application thereof". Paragraph 0045-0048; 0186-0189. . Retrieved 2019/12/02.
• 2、 -. "Esters and amides of substituted indenyl acetic acids". . . Retrieved 2008/06/13.