(2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Base Information

• Chemical Name: (2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
• CAS No.: 136124-31-7
• Molecular Formula: C₂₀H₂₉N₃O₆S₂
• Molecular Weight: 471.599
• Mol file: 136124-31-7.mol

Synonyms:(2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property of (2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

There total 11 articles about (2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-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:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (2R,4S)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (136124-31-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / CBr₄, P(Ph₃) / CH₂Cl₂ / 16 h / 22 °C

2: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

3: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

4: 95 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 22 °C / 23271.7 Torr

5: 1.00 M NaOH / ethanol / 12 h / Heating

With sodium hydroxide; carbon tetrabromide; hydrogen; tetra-n-butylammonium cyanide; triphenylphosphine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

Reference yield:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (2R,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (136124-31-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / pyridine / 22 °C

2: 72 percent / dimethylformamide / 20 h / 55 °C

3: 100 percent / NaOH / H₂O; methanol

4: 40 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 22 °C / 23271.7 Torr

5: 1.00 M NaOH / ethanol / 12 h / Heating

With pyridine; sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00009a016

Reference yield:

(2S,4S)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (132622-71-0) → (2S,4R)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (136124-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 16 h / 22 °C / 23271.7 Torr

2: 1.00 M NaOH / ethanol / 12 h / Heating

With sodium hydroxide; hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jo00009a016

upstream raw materials:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester

(2R,4R)-4-cyano-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

(4R)-1-(tert-butoxycarbonyl)-4-cyano-D-proline ethyl ester

Downstream raw materials:

(4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline

(4S)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-L-proline

(4S)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline