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

Base Information

• Chemical Name: (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline
• CAS No.: 132622-87-8
• Molecular Formula: C₁₉H₂₈N₄O₆S
• Molecular Weight: 440.521
• Mol file: 132622-87-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline 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,4S)-4-[({Methylsulfanyl-[(E)-toluene-4-sulfonylimino]-methyl}-amino)-methyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (136124-31-7) → (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline (132622-87-8)

Guidance literature:

With ammonia; silver nitrate; triethylamine; In acetonitrile; at 22 ℃; for 18h; Yield given;

DOI:10.1021/jo00009a016

Reference yield:

(2R,4R)-4-hydroxyproline-1,2-dicarboxylic acid 1-tert-butyl 2-ethyl ester (77450-00-1) → (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline (132622-87-8)

Guidance literature:

Multi-step reaction with 6 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

6: NH₃, AgNO₃, Et₃N / acetonitrile / 18 h / 22 °C

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

DOI:10.1021/jo00009a016

Reference yield:

(4S)-1-(tert-butoxycarbonyl)-4-bromo-D-proline ethyl ester (132622-76-5) → (4R)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-D-proline (132622-87-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 22 percent / n-Bu₄NCN / dimethylformamide / 20 h / 55 °C

2: 90 percent / 1M NaOH / methanol; H₂O / 22 °C

3: 95 percent / H₂ / 10percent Pd/C / H₂O; ethanol / 22 °C / 23271.7 Torr

4: 1.00 M NaOH / ethanol / 12 h / Heating

5: NH₃, AgNO₃, Et₃N / acetonitrile / 18 h / 22 °C

With sodium hydroxide; ammonia; hydrogen; tetra-n-butylammonium cyanide; silver nitrate; triethylamine; palladium on activated charcoal; In methanol; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00009a016

upstream raw materials:

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

(4R)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-D-proline

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

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