(2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester

Base Information

• Chemical Name: (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester
• CAS No.: 127700-58-7
• Molecular Formula: C₁₈H₂₉NO₄S
• Molecular Weight: 355.499
• Mol file: 127700-58-7.mol

Synonyms:(2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester

Chemical Property of (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester

There total 5 articles about (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl 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: 47.0%

butyl magnesium bromide (693-04-9) + 1-p-toluensulfonylaziridine-(2S)-carboxylic acid tert-butyl ester (127700-57-6) → 3-(N-para-toluenesulphonylamino)propanoic acid tert-butyl ester + (2R)-(N-para-toluenesulphonylaminomethyl)hexanoic acid tert-butyl ester + (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester (127700-58-7)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In tetrahydrofuran; at -25 ℃; for 2h;

DOI:10.1016/S0040-4020(01)87968-0

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester (127700-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) potassium carbonate / 1) CH₂Cl₂, 0 deg C, 15 min, 2) r.t., 2 h

2: 96 percent / lithium hydroxide monohydrate / H₂O; dioxane / 0.25 h / 0 °C

3: 86 percent / boron trifluoride etherate / CH₂Cl₂; cyclohexane / 0.17 h

4: 50 percent / CuBr*SMe₂, SMe₂ / tetrahydrofuran / 2 h / -25 °C

With lithium hydroxide; copper(I) bromide dimethylsulfide complex; dimethylsulfide; boron trifluoride diethyl etherate; potassium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; water;

DOI:10.1016/S0040-4020(01)87968-0

Reference yield:

(2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid (88452-86-2) → (2S)-N-para-toluenesulphonylaminoheptanoic acid tert-butyl ester (127700-58-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / boron trifluoride etherate / CH₂Cl₂; cyclohexane / 0.17 h

2: 50 percent / CuBr*SMe₂, SMe₂ / tetrahydrofuran / 2 h / -25 °C

With copper(I) bromide dimethylsulfide complex; dimethylsulfide; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1016/S0040-4020(01)87968-0

upstream raw materials:

butyl magnesium bromide

1-p-toluensulfonylaziridine-(2S)-carboxylic acid tert-butyl ester

p-toluenesulfonyl chloride

(2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid

Downstream raw materials:

(2S)-2-aminoheptanoic acid

Refernces

• 1、 Baldwin, Jack E.,Adlington, Robert M.,O'Neil, Ian A.,Schofield, Christopher,Spivey, Alan C.,Sweeney, Joseph B.. "The Ring Opening of Aziridine-2-carboxylate Esters with Organometallic Reagents". . p. 1852 - 1854. Retrieved 2007/10/02.