N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester

Base Information

• Chemical Name: N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester
• CAS No.: 130830-71-6
• Molecular Formula: C₁₆H₁₉NO₆
• Molecular Weight: 321.33
• Mol file: 130830-71-6.mol

Synonyms:N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester

Chemical Property of N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester

There total 4 articles about N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl 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: 94.0%

methanol (67-56-1) + N-(benzyloxycarbonyl)-trans-4-cyano-D-proline ethyl ester (130830-67-0) → N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester (130830-71-6)

Guidance literature:

With hydrogenchloride; for 96h;

DOI:10.1021/jm00106a037

Reference yield:

(2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine (130930-27-7) → N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester (130830-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / pyridine / CHCl₃ / 168 h / Ambient temperature

2: 72 percent / dimethylsulfoxide / 4 h / 80 °C

3: 94 percent / HCl / 96 h

With pyridine; hydrogenchloride; In chloroform; dimethyl sulfoxide;

DOI:10.1021/jm00106a037

Reference yield:

cis-hydroxy-D-proline (2584-71-6,30724-02-8) → N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline dimethyl ester (130830-71-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / NaHCO₃ / H₂O; toluene / 16.5 h / Ambient temperature

2: 100 percent / p-toluenesulfonic acid / 16 h / Heating

3: 92 percent / pyridine / CHCl₃ / 168 h / Ambient temperature

4: 72 percent / dimethylsulfoxide / 4 h / 80 °C

5: 94 percent / HCl / 96 h

With pyridine; hydrogenchloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; In chloroform; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jm00106a037

upstream raw materials:

methanol

N-(benzyloxycarbonyl)-trans-4-cyano-D-proline ethyl ester

(2R,4R)-2-ethoxycarbonyl-4-hydroxy-N-(benzyloxycarbonyl)pyrrolidine

cis-hydroxy-D-proline

Downstream raw materials:

N-(benzyloxycarbonyl)-trans-4-carboxy-D-proline

trans-4-carboxy-D-proline

Mosher amide of trans-4-carboxy-D-proline dimethyl ester