3-Isoquinolinecarboxylic acid, 2-[(2S)-3-(3,4-dimethoxyphenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino ]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, methyl ester, (3S)-

Base Information

• Chemical Name: 3-Isoquinolinecarboxylic acid, 2-[(2S)-3-(3,4-dimethoxyphenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino ]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, methyl ester, (3S)-
• CAS No.: 538367-15-6
• Molecular Formula: C29H38N2O9
• Molecular Weight: 558.629
• Mol file: 538367-15-6.mol

Synonyms:

Chemical Property of 3-Isoquinolinecarboxylic acid, 2-[(2S)-3-(3,4-dimethoxyphenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino ]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, methyl ester, (3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Isoquinolinecarboxylic acid, 2-[(2S)-3-(3,4-dimethoxyphenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino ]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, methyl ester, (3S)-

There total 7 articles about 3-Isoquinolinecarboxylic acid, 2-[(2S)-3-(3,4-dimethoxyphenyl)-2-[[(1,1-dimethylethoxy)carbonyl]amino ]-1-oxopropyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-, methyl ester, (3S)- 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: 80.0%

methyl (S)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate (175673-28-6) + (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid (127095-97-0) → (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (538367-15-6)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; for 4h;

DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

levodopa (59-92-7,90638-38-3) → (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (538367-15-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 75 percent / H₂SO₄; water / 24 h

2.1: 99 percent / HCl / 6 h / Heating

3.1: Ac₂O / 4 h

3.2: 87 percent / water / methanol

4.1: 90 percent / K₂CO₃ / acetone / Heating

5.1: 85 percent / HCl / methanol / 4 h / Heating

6.1: 80 percent / bis(2-oxo-3-oxazolidinyl) phosphinic chloride; Et₃N / CH₂Cl₂ / 4 h

With hydrogenchloride; sulfuric acid; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; acetic anhydride; potassium carbonate; triethylamine; In methanol; dichloromethane; acetone; 1.1: Pictet-Spengler cyclization;

DOI:10.1016/S0040-4039(03)01785-4

Reference yield:

(S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester (138908-56-2) → (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(3,4-dimethoxy-phenyl)-propionyl]-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid methyl ester (538367-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / KOH; water / methanol

2: 80 percent / bis(2-oxo-3-oxazolidinyl) phosphinic chloride; Et₃N / CH₂Cl₂ / 4 h

With potassium hydroxide; water; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(03)01785-4

upstream raw materials:

methyl (S)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylate

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,4-dimethoxyphenyl)propanoic acid

levodopa

(S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester

Downstream raw materials:

(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-1-hydroxy-8,9-dimethoxy-4-oxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

(3S,11aS)-3-(3,4-Dimethoxy-benzyl)-8,9-dimethoxy-1,4-dioxo-1,3,4,6,11,11a-hexahydro-pyrazino[1,2-b]isoquinoline-2-carboxylic acid isopropyl ester

3-(3,4-dimethoxy-benzyl)-8,9-dimethoxy-2,3,11,11a-tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione