[(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester
• CAS No.: 182268-04-8
• Molecular Formula: C₃₁H₃₉N₃O₅
• Molecular Weight: 533.668
• Mol file: 182268-04-8.mol

Synonyms:[(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester

Chemical Property of [(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester

There total 1 articles about [(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic 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: 43.0%

L-phenylalanine cyclohexylamide (17186-53-7,92698-80-1) + (4-Iodomethyl-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-acetic acid tert-butyl ester → [(R)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester (182176-20-1) + [(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester (182268-04-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In various solvent(s); at 80 ℃; for 32h; in NMP;

DOI:10.1002/hlca.19960790508

Reference yield:

[(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester (182268-04-8) → Benzoic acid (S)-3-amino-1-((S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl)-2,5-dioxo-pyrrolidin-3-ylmethyl ester (182176-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) CF₃COOH 2.) SOCl₂ / 1.) CH₂Cl₂, r.t., 5 h 2.) CH₂Cl₂, r.t., 15 h

2: 87 percent / 2 N HCl / dioxane / 3 h / Ambient temperature

With hydrogenchloride; thionyl chloride; trifluoroacetic acid; In 1,4-dioxane;

DOI:10.1002/hlca.19960790508

Reference yield:

[(S)-4-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-4,5-dihydro-oxazol-4-yl]-acetic acid tert-butyl ester (182268-04-8) → {(S)-1-[(S)-1-((S)-1-Cyclohexylcarbamoyl-2-phenyl-ethyl)-3-hydroxymethyl-2,5-dioxo-pyrrolidin-3-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CF₃COOH 2.) SOCl₂ / 1.) CH₂Cl₂, r.t., 5 h 2.) CH₂Cl₂, r.t., 15 h

2: 87 percent / 2 N HCl / dioxane / 3 h / Ambient temperature

3: 86 percent / HATU, HOAT, Et(i-Pr)2N / dimethylformamide / 2 h / Ambient temperature

4: 88 percent / NaCN / methanol / 1.5 h / 60 °C / in a sealed tube

With hydrogenchloride; thionyl chloride; 1-hydroxy-7-aza-benzotriazole; sodium cyanide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19960790508

upstream raw materials:

L-phenylalanine cyclohexylamide

Downstream raw materials:

(S)-N-Cyclohexyl-2-((S)-6,8-dioxo-2-phenyl-3-oxa-1,7-diaza-spiro[4.4]non-1-en-7-yl)-3-phenyl-propionamide

Benzoic acid (S)-3-amino-1-((S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl)-2,5-dioxo-pyrrolidin-3-ylmethyl ester

Benzoic acid (S)-3-((S)-2-tert-butoxycarbonylamino-propionylamino)-1-((S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl)-2,5-dioxo-pyrrolidin-3-ylmethyl ester

Benzoic acid (S)-3-benzoylamino-1-((S)-1-cyclohexylcarbamoyl-2-phenyl-ethyl)-2,5-dioxo-pyrrolidin-3-ylmethyl ester