(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide

Base Information

• Chemical Name: (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide
• CAS No.: 1287731-48-9
• Molecular Formula: C₁₈H₂₂N₂O₄S
• Molecular Weight: 362.45
• Mol file: 1287731-48-9.mol

Synonyms:(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide

Chemical Property of (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide

There total 1 articles about (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide 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: 86.0%

(SS,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide (507453-94-3) → (R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide (1287731-48-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 ℃; for 8h;

DOI:10.1021/jo2002352

Reference yield: 37.0%

(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide (1287731-48-9) + methyl iodide (74-88-4) → (2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide (943241-46-1) + (2S,3R)-(+)-N-methoxy-N,2-dimethyl-3-phenyl-3-(tosylamino)propanamide (1287731-64-9)

Guidance literature:

(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; tert-butyl methyl ether; at -78 - -50 ℃; for 2h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo2002352

Reference yield:

(R)-(+)-N-methoxy-N-methyl-3-phenyl-3-(tosylamino)-propanamide (1287731-48-9) → (2S,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenyl-1-butylpropanone (1287731-65-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine; lithium chloride / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - -50 °C / Inert atmosphere

2.1: tetrahydrofuran; hexane / 1 h / -50 °C / Inert atmosphere

With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane;

DOI:10.1021/jo2002352

upstream raw materials:

(S_S,3R)-(+)-3-[N-(p-toluenesulfinyl)amino]-N-methoxy-N-methyl-3-(phenyl)propionamide

Downstream raw materials:

(2S,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenyl-1-butylpropanone

(2R,3R)-(+)-N-methoxy-N,2-dimethyl-3-(p-toluenesulfonamido)-3-phenylpropanamide

(2S,3R)-(+)-N-methoxy-N,2-dimethyl-3-phenyl-3-(tosylamino)propanamide