Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt

Base Information

• Chemical Name: Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt
• CAS No.: 77497-97-3
• Molecular Formula: C17H17NO2^.C7H8O3S
• Molecular Weight: 439.532
• Hs Code.: 2933499090
• European Community (EC) Number: 406-960-0,616-464-8
• UNII: 7O3F0JS1ZO
• Mol file: 77497-97-3.mol

Synonyms:(S)-1,2,3,4-Tetrahydro-3-isoquinoline-carboxylic acid benzyl ester PTSA salt;(3S)-Benzyl-1,2,3,4-tetrahydroisoquinoleine-3-carboxylate-4-toluenesulfonate;Phenylmethyl(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate;S)-1,2,3,4,-Tetrahydro-3-isoquinolinecarboxylic Acid benzyl ester p-toluenesulfonic acid salt;

Chemical Property of Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt

Chemical Property:

• Appearance/Colour: white crystalline
• Melting Point: 145-150 °C
• Boiling Point: 634.1 °C at 760 mmHg
• Flash Point: 337.3 °C
• PSA: 101.08000
• LogP: 5.09560
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 439.14534407
• Heavy Atom Count: 31
• Complexity: 531

Purity/Quality:

99% ^*data from raw suppliers

Benzyl (S)-(?)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1C(NCC2=CC=CC=C21)C(=O)OCC3=CC=CC=C3
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)O.C1[C@H](NCC2=CC=CC=C21)C(=O)OCC3=CC=CC=C3
• Uses: Quinapril intermediate Used to prepare a novel class of antifungal agents.

Technology Process of Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt

There total 4 articles about Benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate p-toluenesulfonic acid salt 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: 62.2%

p-toluenesulfonic acid monohydrate (6192-52-5) + (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (77497-95-1) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt (77497-97-3)

Guidance literature:

In benzene; for 5h; Heating;

DOI:10.1248/cpb.31.312

Reference yield: 60.0%

toluene-4-sulfonic acid (104-15-4) + (3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride (77497-95-1) + benzyl alcohol (100-51-6,185532-71-2) → benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt (77497-97-3)

Guidance literature:

In benzene; at 80 ℃; for 16h;

DOI:10.1016/0960-894X(96)00222-3

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → benzyl (S)-(-)-1,2,3,4-tetrahydro-3-isoquinoline carboxylate p-toluenesulfonic acid salt (77497-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 75.4 percent / cc. hydrochloric acid / H₂O / 4 h / 95 - 100 °C

2: 62.2 percent / benzene / 5 h / Heating

With hydrogenchloride; In water; benzene;

DOI:10.1248/cpb.31.312

upstream raw materials:

p-toluenesulfonic acid monohydrate

(3S)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

benzyl alcohol

L-phenylalanine

Downstream raw materials:

(S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, phenylmethylester

benzyl (3S)-2-(3-benzoylthio-2-methylpropionyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

(S)-N-[(1S)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide

(S)-N-[(1R)-1-phenylethyl]-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-3-thiocarboxamide