(2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Base Information

• Chemical Name: (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
• CAS No.: 305322-30-9
• Molecular Formula: C₂₄H₂₃N₃O₅
• Molecular Weight: 433.464
• Mol file: 305322-30-9.mol

Synonyms:(2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Chemical Property of (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

There total 4 articles about (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole 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:

(1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline (305322-27-4) → (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (305322-30-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h / 20 °C / 1551.49 Torr

2: 93 percent / xylene / 2 h / Heating

3: TFA / CH₂Cl₂ / 1 h / 20 °C

4: TEA / CH₂Cl₂ / 20 °C

With TEA; hydrogen; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; xylene;

DOI:10.1021/jm000959x

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + 2-amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid methyl ester → (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (305322-30-9)

Guidance literature:

With TEA; In dichloromethane; at 20 ℃;

DOI:10.1021/jm000959x

Reference yield:

(2R,5R,11bS)-2-(tert-butoxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (305322-29-6) → (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (305322-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 1 h / 20 °C

2: TEA / CH₂Cl₂ / 20 °C

With TEA; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm000959x

upstream raw materials:

benzyl chloroformate

(2R,5R,11bS)-2-(tert-butoxycarbonyl)amino-5-methoxycarbonyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

(1S,3R,2'R)-1-[2'-(tert-butoxycarbonyl)amino-2'-carboxyethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

(1S,3R,2'R)-2-benzyl-1-[2'-benzyloxycarbonyl-2'-(tert-butoxycarbonyl)aminoethyl]-3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline

Downstream raw materials:

(R)-2-[((2R,5R,11bS)-2-Benzyloxycarbonylamino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

(S)-3-[((2R,5R,11bS)-2-Benzyloxycarbonylamino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-4-phenyl-butyric acid methyl ester

(R)-3-[((2R,5R,11bS)-2-Benzyloxycarbonylamino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-4-phenyl-butyric acid methyl ester

(2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole