(+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide

Base Information

• Chemical Name: (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide
• CAS No.: 869468-27-9
• Molecular Formula: C₂₅H₃₄N₂O₄
• Molecular Weight: 426.556
• Mol file: 869468-27-9.mol

Synonyms:(+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide

Chemical Property of (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide

There total 5 articles about (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide 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:

(S)-3-Amino-4,4-dimethyl-pentanoic acid ((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide + dibenzyl dicarbonate (31139-36-3) → (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide (869468-27-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 18h;

DOI:10.1021/jo051207j

Reference yield:

pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) → (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide (869468-27-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Et₃N / tetrahydrofuran / 1.5 h / -20 °C

2: 60 percent / TMEDA / tetrahydrofuran / -105 °C

3: H₂ / Pd/C / ethanol / 18 h / 3361.46 Torr

4: 0.25 g / NaOH / dioxane; H₂O / 18 h / 20 °C

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

DOI:10.1021/jo051207j

Reference yield:

(E)-4,4-dimethyl-2-pentenoyl chloride (132278-01-4) → (+)-(1'S,2'S,3S)-3-(benzyloxycarbonyl)amino-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpentanamide (869468-27-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Et₃N / tetrahydrofuran / 1.5 h / -20 °C

2: 60 percent / TMEDA / tetrahydrofuran / -105 °C

3: H₂ / Pd/C / ethanol / 18 h / 3361.46 Torr

4: 0.25 g / NaOH / dioxane; H₂O / 18 h / 20 °C

With sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

DOI:10.1021/jo051207j

upstream raw materials:

dibenzyl dicarbonate

pseudoephedrine

(E)-4,4-dimethyl-2-pentenoyl chloride

E-(+)-(1'S,2'S)-N-methyl-N-(2'-phenyl-2'-hydroxy-1'-methylethyl)-4,4-dimethylpent-2-enamide

Downstream raw materials:

(-)-(3S)-3-((benzyloxycarbonyl)amino)-4,4-dimethylpentanol