methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Base Information

• Chemical Name: methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate
• CAS No.: 643014-01-1
• Molecular Formula: C₂₄H₂₉F₃N₂O₆
• Molecular Weight: 498.499
• Mol file: 643014-01-1.mol

Synonyms:methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Chemical Property of methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

There total 5 articles about methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate 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: 91.0%

(S)-N-benzyl-5-thioxoproline tert-butyl ester (90741-31-4) + methyl (2S)-5-bromo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (161553-09-9) → methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (643014-01-1)

Guidance literature:

With triethylamine; triphenylphosphine; In acetonitrile; at 20 ℃;

DOI:10.1016/j.tetlet.2003.09.170

Reference yield:

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (88668-76-2) → methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (643014-01-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrobromic acid; CHCl₃ / 20 °C

2.1: 80 percent / LiBr / acetone / 79 h / 20 °C

3.1: acetonitrile / 46 h / 20 °C

3.2: 91 percent / PPh₃; Et₃N / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

With chloroform; hydrogen bromide; lithium bromide; In acetone; acetonitrile; 2.1: Finkelstein reaction / 3.1: Eschenmoser olefination / 3.2: Eschenmoser olefination;

DOI:10.1016/j.tet.2004.09.037

Reference yield:

methyl (2S)-5-chloro-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (831242-10-5) → methyl (2S)-5-[(2S)-1-benzyl-2-tert-butoxycarbonyl-5-pyrrolidinylidenyl]-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (643014-01-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / LiBr / acetone / 79 h / 20 °C

2.1: acetonitrile / 46 h / 20 °C

2.2: 91 percent / PPh₃; Et₃N / acetonitrile; CH₂Cl₂ / 24 h / 20 °C

With lithium bromide; In acetone; acetonitrile; 1.1: Finkelstein reaction / 2.1: Eschenmoser olefination / 2.2: Eschenmoser olefination;

DOI:10.1016/j.tet.2004.09.037

upstream raw materials:

(S)-N-benzyl-5-thioxoproline tert-butyl ester

methyl (2S)-5-bromo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

methyl (2S)-5-chloro-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate

Downstream raw materials:

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-(2-benzyloxycarbonylaminoacetamido)-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-(9H)-fluoren-9-ylmethoxycarbonylamino-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate

diphenylmethyl (3S,6S,9aS)-6-[(2S)-2-((2S)-2-((2S)-2-amino-4-methylpentanamido)-4-tert-butoxycarbonylpropanamido)-3-methylbutanamido]-5-oxo-octahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate