(3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester

Base Information

• Chemical Name: (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester
• CAS No.: 440370-42-3
• Molecular Formula: C₃₁H₃₇NO₇
• Molecular Weight: 535.637
• Mol file: 440370-42-3.mol

Synonyms:(3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester

Chemical Property of (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester

There total 5 articles about (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester 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%

(E)-4-(4-methoxy-phenoxy)-but-2-enoic acid methyl ester (96821-35-1) + (1R,2R)-N-(2-hydroxymethyl-2-phenylethyl)-N-methyl-(4-methoxy-phenyl)acetamide (440370-31-0) → (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester (440370-42-3)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.666667h;

DOI:10.1021/ol0259847

Reference yield:

(1R,2R)-pseudoephedrine (321-97-1,7009-81-6,90-83-5,6912-63-6) → (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester (440370-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / aq. NaOH / isopropyl acetate / 21 h / 0 °C

2: lithium bis(trimethylsilyl)amide; N,N,N,N-tetramethylethylenediamine / tetrahydrofuran / 0.67 h / -78 °C

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; Isopropyl acetate; 2: Michael addition;

DOI:10.1021/jo035564a

Reference yield:

4-methoxyphenyl-acetic chloride (4693-91-8) → (3R,4R)-4-(4-methoxyphenyl)-4-[(1R,2R)-(2-hydroxy-1-methyl-2-phenylethyl)-methylcarbamoyl]-3-(4-methoxyphenoxymethyl)-butyric acid methyl ester (440370-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / aq. NaOH / isopropyl acetate / 21 h / 0 °C

2: lithium bis(trimethylsilyl)amide; N,N,N,N-tetramethylethylenediamine / tetrahydrofuran / 0.67 h / -78 °C

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; Isopropyl acetate; 2: Michael addition;

DOI:10.1021/jo035564a

upstream raw materials:

(E)-4-(4-methoxy-phenoxy)-but-2-enoic acid methyl ester

(1R,2R)-N-(2-hydroxymethyl-2-phenylethyl)-N-methyl-(4-methoxy-phenyl)acetamide

methyl-4-bromo-2-butenoate

(1R,2R)-pseudoephedrine