4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 207126-23-6
• Molecular Formula: C₃₅H₅₀N₆O₈
• Molecular Weight: 682.817
• Mol file: 207126-23-6.mol

Synonyms:4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

There total 2 articles about 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic 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: 95.0%

tert-butyl 2-N-carbobenzoxy-(S)-2,3-diaminopropionate (77215-55-5) + 5-[2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-ethyl]-4-oxo-5,6,7,8-tetrahydro-4H-1,5,8a-triaza-azulene-2-carboxylic acid (163213-40-9) → 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (207126-23-6)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; for 8.5h; Ambient temperature;

DOI:10.1002/(SICI)1099-1344(199804)41:4<273::AID-JLCR76>3.0.CO;2-1

Reference yield:

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid (35761-26-3) → 4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (207126-23-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / aq. H₂SO₄ / dioxane / 60 h / Ambient temperature

2: 95 percent / EDC, HOBT / CH₂Cl₂ / 8.5 h / Ambient temperature

With sulfuric acid; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1002/(SICI)1099-1344(199804)41:4<273::AID-JLCR76>3.0.CO;2-1

Reference yield:

4-{2-[2-((S)-2-Benzyloxycarbonylamino-2-tert-butoxycarbonyl-ethylcarbamoyl)-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (207126-23-6) → 4-(2-{2-[(S)-2-Carboxy-2-(toluene-4-sulfonylamino)-ethylcarbamoyl]-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (163213-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / H₂ / Pd/C / methanol / 12.5 h

2: 77 percent / pyridine / ethyl acetate / 12.5 h / Heating

3: CF₃COOH / CH₂Cl₂ / 3.5 h / 0 °C

4: Et₃N, H₂ / Pd(OH)2/C / H₂O / 2.5 h / Ambient temperature

With pyridine; hydrogen; triethylamine; trifluoroacetic acid; palladium dihydroxide; palladium on activated charcoal; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1002/(SICI)1099-1344(199804)41:4<273::AID-JLCR76>3.0.CO;2-1

upstream raw materials:

tert-butyl 2-N-carbobenzoxy-(S)-2,3-diaminopropionate

5-[2-(1-tert-Butoxycarbonyl-piperidin-4-yl)-ethyl]-4-oxo-5,6,7,8-tetrahydro-4H-1,5,8a-triaza-azulene-2-carboxylic acid

(S)-3-amino-2-(((benzyloxy)carbonyl)amino)propanoic acid

Downstream raw materials:

4-(2-{2-[(S)-2-Carboxy-2-(toluene-4-sulfonylamino)-ethylcarbamoyl]-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

4-(2-{2-[(S)-2-(2-Bromo-4-methyl-benzenesulfonylamino)-2-tert-butoxycarbonyl-ethylcarbamoyl]-4-oxo-7,8-dihydro-4H,6H-1,5,8a-triaza-azulen-5-yl}-ethyl)-piperidine-1-carboxylic acid tert-butyl ester