(2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide

Base Information

• Chemical Name: (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide
• CAS No.: 272458-93-2
• Molecular Formula: C₁₈H₂₆N₂O₄S
• Molecular Weight: 366.481
• Mol file: 272458-93-2.mol

Synonyms:(2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide

Chemical Property of (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide

There total 2 articles about (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide 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%

(1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane (208516-68-1) + (S)-N-methoxy-N-methyl-2-(toluene-4-sulfonylamino)-propionamide (1019853-13-4) → (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide (272458-93-2)

Guidance literature:

(S)-N-methoxy-N-methyl-2-(toluene-4-sulfonylamino)-propionamide; With sodium hydride; In tetrahydrofuran;

(1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane; With triphenylphosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0957-4166(00)00006-9

Reference yield:

(S)-N-tosylalanine methyl ester (59724-69-5) → (2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide (272458-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / pyridine; DCC / CH₂Cl₂

2.1: NaH / tetrahydrofuran

2.2: 86 percent / Pd(dba)2; PPh₃ / tetrahydrofuran / 20 °C

With pyridine; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Metallation / 2.2: amination;

DOI:10.1016/S0957-4166(00)00006-9

Reference yield:

(2S,2'S)-N'-methyl-N'-methoxy-N-[2-(2-methylcyclopropylidene)ethyl]-N-tosyl-L-alaninamide (272458-93-2) → (2S,2'S)-2-{N-[2-(2-methylcyclopropylidene)ethyl]-N-tosylamino}propanal (272458-95-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.666667h;

DOI:10.1016/S0957-4166(00)00006-9

upstream raw materials:

(1R,2S)-2-methyl-1-tosyloxy-1-vinylcyclopropane

(S)-N-methoxy-N-methyl-2-(toluene-4-sulfonylamino)-propionamide

(S)-N-tosylalanine methyl ester

Downstream raw materials:

(2S,2'S)-2-{N-[2-(2-methylcyclopropylidene)ethyl]-N-tosylamino}propanal