methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate

Base Information

• Chemical Name: methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate
• CAS No.: 538335-95-4
• Molecular Formula: C₃₅H₃₇N₅O₇
• Molecular Weight: 639.708
• Mol file: 538335-95-4.mol

Synonyms:methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate

Chemical Property of methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate

There total 10 articles about methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate 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:

1-(pyridin-4-yl)piperidine-4-carboxylic acid hydrochloride (210962-09-7) + methyl 2-acetamido-3-[(2-amino-3-benzyloxycarbonylpropoxy)-4-cyanophenyl]acrylate hydrochloride → methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate (538335-95-4)

Guidance literature:

With triethylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm020485x

Reference yield:

4-benzyl Boc-D-aspartate (51186-58-4,98482-77-0) → methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate (538335-95-4)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / tetrahydrofuran / 0.17 h / 0 °C

2: 5.28 g / aq. NaBH₄ / tetrahydrofuran / 0.05 h / 0 °C

3: 67 percent / N,N,N',N'-tetramethylazodicarboxamide; triphenylphosphine / toluene / 0 °C

4: 79 percent / triethylamine; tri-o-tolylphosphine; Pd(OAc)2 / acetonitrile / Heating

5: 100 percent / HCl / dioxane

6: triethylamine; bromotripyrrolidinophosphonium hexafluorophosphate / dimethylformamide / 20 °C

With hydrogenchloride; palladium diacetate; sodium tetrahydroborate; diamide; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene; acetonitrile; 4: Heck reaction;

DOI:10.1021/jm020485x

Reference yield:

(R)-3-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid benzyl ester (182748-72-7) → methyl 2-acetamido-3-[2-[(R)-2-[1-(4-pyridyl)piperidine-4-carbonyl]amino-3-benzyloxycarbonylpropoxy]-4-cyanophenyl]acrylate (538335-95-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / N,N,N',N'-tetramethylazodicarboxamide; triphenylphosphine / toluene / 0 °C

2: 79 percent / triethylamine; tri-o-tolylphosphine; Pd(OAc)2 / acetonitrile / Heating

3: 100 percent / HCl / dioxane

4: triethylamine; bromotripyrrolidinophosphonium hexafluorophosphate / dimethylformamide / 20 °C

With hydrogenchloride; palladium diacetate; diamide; triethylamine; triphenylphosphine; tris-(o-tolyl)phosphine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide; toluene; acetonitrile; 2: Heck reaction;

DOI:10.1021/jm020485x

upstream raw materials:

1-(pyridin-4-yl)piperidine-4-carboxylic acid hydrochloride

4-benzyl Boc-D-aspartate

(R)-3-((tert-butoxycarbonyl)amino)-4-hydroxybutyric acid benzyl ester

3-hydroxy-4-iodobenzonitrile