(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid

Base Information

• Chemical Name: (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid
• CAS No.: 129982-29-2
• Molecular Formula: C₃₀H₄₁NO₄
• Molecular Weight: 479.66
• Mol file: 129982-29-2.mol

Synonyms:(S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid

Chemical Property of (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid

There total 5 articles about (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid 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:

cyclopentanecarboxylic acid (3400-45-1) + 2-{[Bis-((S)-1-phenyl-ethyl)-amino]-methyl}-acrylic acid tert-butyl ester (137219-70-6) → (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid (129982-29-2)

Guidance literature:

With lithium diisopropyl amide; Yield given. Multistep reaction; 1) 0 deg C, 1 h, 2) - 50 to - 20 deg C, 6 h;

DOI:10.1016/S0040-4039(00)91786-6

Reference yield:

(1S,1'S)-bis(1-phenylethyl)amine (21003-56-5,21003-57-6,23294-41-9,42287-48-9,56210-72-1,10024-74-5) → (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid (129982-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / K₂CO₃ / acetonitrile / 18 h / 60 - 70 °C

2: 1) LDA / 1) 0 deg C, 1 h, 2) - 50 to - 20 deg C, 6 h

With potassium carbonate; lithium diisopropyl amide; In acetonitrile;

DOI:10.1016/S0040-4039(00)91786-6

Reference yield:

tert-butyl 2-hydroxymethylacrylate (121065-74-5) → (S,S,S)-1-{3-[bis(1-phenylethyl)amino]-2-(tert-butoxycarbonyl)propyl}-1-cyclopentylcarboxylic acid (129982-29-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; triethylamine; thionyl chloride / toluene / 0 - 50 °C

2: toluene / 35 - 45 °C / Large scale

3: lithium diisopropyl amide / tetrahydrofuran / -30 - 20 °C / Large scale

With pyridine; thionyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; toluene; 3: |Michael Addition;

DOI:10.1021/op020091f

upstream raw materials:

cyclopentanecarboxylic acid

2-{[Bis-((S)-1-phenyl-ethyl)-amino]-methyl}-acrylic acid tert-butyl ester

(1S,1'S)-bis(1-phenylethyl)amine

tert-butyl 2-(bromomethyl)acrylate

Downstream raw materials:

tert-butyl (S,S)-N-{1-[3-amino-2-(tert-butoxycarbonyl)-propyl]-1-cyclopentylcarbonyl}-O₄-tert-butyltyrosinate

(S,S,S)-N-{1-[2-carboxy-3-(N-mesyllysylamino)propyl]-1-cyclopentylcarbonyl}tyrosine