5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester
• CAS No.: 162612-34-2
• Molecular Formula: C₃₀H₄₀N₂O₇
• Molecular Weight: 540.657
• Mol file: 162612-34-2.mol

Synonyms:5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property of 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

There total 4 articles about 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic 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: 82.0%

t-butyl 5-iodo-3-(2-methoxycarbonylethyl)-4-methylpyrrole-2-carboxylate (31837-48-6) + 2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid N-(4'-methoxybenzyl)amide (162612-32-0) → 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (162612-34-2)

Guidance literature:

With copper(l) iodide; palladium;

DOI:10.1016/0040-4039(95)00032-8

Reference yield:

4-methoxy-benzylamine (2393-23-9) → 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (162612-34-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tetrahydrofuran / 144 h / Ambient temperature

2: 82 percent / Pd(Ph₃P)4, CuI, Et₃N / dimethylformamide / 21 h / Ambient temperature

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo970289b

Reference yield:

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid (145071-98-3) → 5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-4-(4-methoxy-benzylcarbamoyl)-pent-1-ynyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (162612-34-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / P₄S₁₀ / CH₂Cl₂ / 40 h / Ambient temperature

2: 90 percent / tetrahydrofuran / 144 h / Ambient temperature

3: 82 percent / Pd(Ph₃P)4, CuI, Et₃N / dimethylformamide / 21 h / Ambient temperature

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetraphosphorus decasulfide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo970289b

upstream raw materials:

t-butyl 5-iodo-3-(2-methoxycarbonylethyl)-4-methylpyrrole-2-carboxylate

2(R)-methyl-3(R)-<1'(S)-hydroxyethyl>-4-pentynoic acid N-(4'-methoxybenzyl)amide

4-methoxy-benzylamine

(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid

Downstream raw materials:

5-[(3R,4R)-3-((S)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-methyl-5-oxo-pyrrolidin-(2Z)-ylidenemethyl]-3-(2-methoxycarbonyl-ethyl)-4-methyl-1H-pyrrole-2-carboxylic acid tert-butyl ester