rac 5-Carboxy Tolterodine

Base Information

• Chemical Name: rac 5-Carboxy Tolterodine
• CAS No.: 1076199-77-3
• Molecular Formula: C22H29NO3
• Molecular Weight: 355.477
• DSSTox Substance ID: DTXSID50435500
• Mol file: 1076199-77-3.mol

Synonyms:rac 5-Carboxy Tolterodine;1076199-77-3;rac5-CarboxyTolterodine-d14;3-[3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzoic acid;5-Carboxy Tolterodine;rac-5-carboxy Tolterodine;SCHEMBL1116312;3-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-hydroxybenzoic acid;SCHEMBL15160497;DTXSID50435500;3-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzoic Acid;AKOS025294055;CS-T-10540;FT-0664373;J-001979

Chemical Property of rac 5-Carboxy Tolterodine

Chemical Property:

• PSA: 60.77000
• LogP: 4.73120
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 355.21474379
• Heavy Atom Count: 26
• Complexity: 423

Purity/Quality:

99% ^*data from raw suppliers

5-Carboxytolterodineformate 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)N(CCC(C1=CC=CC=C1)C2=C(C=CC(=C2)C(=O)O)O)C(C)C
• Uses: A metabolite of Tolterodine (T535800). Also, a degradation product of Fesoterodine (F321300) formed under stress conditions in tablet dosage forms.

Technology Process of rac 5-Carboxy Tolterodine

There total 19 articles about rac 5-Carboxy Tolterodine 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:

(R)-N,N-diisopropyl-3-phenyl-3-(5-formyl-2-hydroxyphenyl)propyl-1-amine (214601-12-4) → racemic 3-(3-N,N'-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoic acid (1076199-77-3)

Guidance literature:

With hydrogen; 5%-palladium/activated carbon; In methanol; at 25 - 30 ℃; for 8h; under 2206.72 - 2942.29 Torr; autoclave;

Reference yield:

N,N-diisopropyl-3-phenyl-2-propen-1-amine (87462-12-2) + 4-hydroxy-benzoic acid (99-96-7) → racemic 3-(3-N,N'-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoic acid (1076199-77-3)

Guidance literature:

With sulfuric acid; acetic acid; In n-heptane; at 80 - 85 ℃;

Reference yield:

(+/-)-N,N-diisopropyl-3-(2-benzyloxy-5-bromophenyl)-3-phenylpropylamine → racemic 3-(3-N,N'-diisopropylamino-1-phenyl-propyl)-4-hydroxy-benzoic acid (1076199-77-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 0.75 h / -65 - -55 °C

2.1: D-tartaric acid / isopropyl alcohol / 16 h / 30 - 35 °C

2.2: 10 - 15 °C

3.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave

4.1: hydrogen / 5%-palladium/activated carbon / methanol / 8 h / 25 - 30 °C / 2206.72 - 2942.29 Torr / autoclave

With n-butyllithium; D-tartaric acid; hydrogen; 5%-palladium/activated carbon; In tetrahydrofuran; methanol; isopropyl alcohol;

upstream raw materials:

N,N-diisopropyl-3-phenyl-2-propen-1-amine

4-hydroxy-benzoic acid

diisopropylamine

cinnamyl chloride

Downstream raw materials:

2-(3-N,N-diisopropylamine-1-phenylpropyl)-4-carboxyphenol isobutyrate

2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxyl-methyl)phenyl isobutyrate

3-(3-(diisopropylamino)-1-phenylpropyl)-4-(methacryloyloxy)benzoic acid

(R)-3-(3-(diisopropylamino)-1-phenylpropyl)-4-(methacryloyloxy)benzoic acid