ETHYL 4-BENZYLOXYCARBONYLAMINO-3-HYDROXY-1-METHYL-1H-PYRROLE-2-CARBOXYLATE

Base Information

• Chemical Name: ETHYL 4-BENZYLOXYCARBONYLAMINO-3-HYDROXY-1-METHYL-1H-PYRROLE-2-CARBOXYLATE
• CAS No.: 212184-25-3
• Molecular Formula: C₁₆H₁₈N₂O₅
• Molecular Weight: 318.329
• Mol file: 212184-25-3.mol

Synonyms:ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate

Chemical Property of ETHYL 4-BENZYLOXYCARBONYLAMINO-3-HYDROXY-1-METHYL-1H-PYRROLE-2-CARBOXYLATE

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ETHYL 4-BENZYLOXYCARBONYLAMINO-3-HYDROXY-1-METHYL-1H-PYRROLE-2-CARBOXYLATE

There total 1 articles about ETHYL 4-BENZYLOXYCARBONYLAMINO-3-HYDROXY-1-METHYL-1H-PYRROLE-2-CARBOXYLATE 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: 53.0%

ethyl 4-carboxy-3-hydroxy-1-methylpyrrole-2-carboxylate (65171-82-6) + benzyl alcohol (100-51-6,185532-71-2) → ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate (212184-25-3)

Guidance literature:

ethyl 4-carboxy-3-hydroxy-1-methylpyrrole-2-carboxylate; With diphenyl-phosphinic acid; triethylamine; In acetonitrile; for 5h; Heating;

benzyl alcohol; In acetonitrile; for 17h; Heating;

DOI:10.1021/ja9930667

Reference yield:

ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate (212184-25-3) + methyl iodide (74-88-4) → Ethyl 4-[(benzyloxycarbonyl)amino]-3-methoxy-1-methyl-1H-pyrrole-2-carboxylate (285137-95-3)

Guidance literature:

With dmap; potassium carbonate; In acetone; at 22 ℃; for 22h;

DOI:10.1021/ja9930667

Reference yield:

ethyl 4-[(benzyloxycarbonyl)amino]-3-hydroxy-1-methylpyrrole-2-carboxylate (212184-25-3) → 4-[(tert-butoxycarbonyl)amino]-3-methoxy-1-methylpyrrole-2-carboxylic acid (212184-27-5)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃; DMAP / acetone / 22 h / 22 °C

2: H₂; DIEA / 10 percent Pd/C / dimethylformamide / 2.1 h

3: 91 percent / aq. NaOH / ethanol / 96 h / 20 °C

With dmap; sodium hydroxide; hydrogen; potassium carbonate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetone; 1: Methylation / 2: Catalytic hydrogenation, acylation / 3: Hydrolysis;

DOI:10.1021/ja9930667

upstream raw materials:

ethyl 4-carboxy-3-hydroxy-1-methylpyrrole-2-carboxylate

benzyl alcohol

Downstream raw materials:

Ethyl 4-[(benzyloxycarbonyl)amino]-3-methoxy-1-methyl-1H-pyrrole-2-carboxylate

4-[(tert-butoxycarbonyl)amino]-3-methoxy-1-methylpyrrole-2-carboxylic acid