(5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one

Base Information

• Chemical Name: (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one
• CAS No.: 1586809-82-6
• Molecular Formula: C₂₁H₁₇F₃N₂O₅
• Molecular Weight: 434.372
• Mol file: 1586809-82-6.mol

Synonyms:(5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one

Chemical Property of (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one

There total 4 articles about (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one 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: 60.0%

methyl (S)-4-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate (119960-01-9) + 2,2,2-trifluoro-N-(2-iodophenyl)acetamide (143321-89-5) → (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one (1586809-82-6)

Guidance literature:

With copper(l) iodide; caesium carbonate; L-proline; In dimethyl sulfoxide; at 50 ℃; for 24h;

DOI:10.1016/j.tetlet.2014.02.059

Reference yield: 47.0%

(4S)-methyl 4-(benzyloxycarbonyl)amino-3-hydroxy-2-(2-trifluoroacetamido)phenyl-2-pentenoate → (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one (1586809-82-6)

Guidance literature:

With caesium carbonate; In methanol; water; at 80 ℃; for 2h;

DOI:10.1016/j.tetlet.2014.02.059

Reference yield:

methyl (S)-4-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate (119960-01-9) → (5S)-1-benzyloxycarbonyl-4-hydroxy-5-methyl-3-(2-trifluoroacetamido)phenyl-3-pyrrolin-2-one (1586809-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: L-proline; copper(l) iodide; caesium carbonate / dimethyl sulfoxide / 72 h / 20 °C

2: caesium carbonate / methanol; water / 2 h / 80 °C

With copper(l) iodide; caesium carbonate; L-proline; In methanol; water; dimethyl sulfoxide; 1: |Heck Reaction;

DOI:10.1016/j.tetlet.2014.02.059

upstream raw materials:

methyl (S)-4-{[(benzyloxy)carbonyl]amino}-3-oxopentanoate

2,2,2-trifluoro-N-(2-iodophenyl)acetamide

Downstream raw materials:

(1'S)-2-[1'-(benzyloxycarbonyl) amino]ethyl-3-methoxycarbonylindole

(1'R)-2-[1'-(benzyloxycarbonyl) amino]ethyl-3-methoxycarbonylindole

C₁₃H₁₁F₃N₂O₃

C₂₃H₂₇N₃O₃