(2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Base Information

• Chemical Name: (2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
• CAS No.: 872035-09-1
• Molecular Formula: C₄₁H₄₄N₆O₇
• Molecular Weight: 732.836

Synonyms:(2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Chemical Property of (2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

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Technology Process of (2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

There total 2 articles about (2S,5S,11bR,1'S)-2-[(N^α-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-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:

(S)-2-[((2S,5S,11bR)-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 (305322-33-2) → (2S,5S,11bR,1'S)-2-[(Nα-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (872035-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / methanol / 5 h / 20 °C / 1551.44 Torr

2: BOP; TEA / CH₂Cl₂

With TEA; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/jm050689o

Reference yield:

(S)-2-[((2S,5S,11bR)-2-Amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carbonyl)-amino]-3-phenyl-propionic acid methyl ester + Boc-Trp-OH (13139-14-5) → (2S,5S,11bR,1'S)-2-[(Nα-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (872035-09-1)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane;

DOI:10.1021/jm050689o

Reference yield: 97.0%

(2S,5S,11bR,1'S)-2-[(Nα-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-methoxycarbonyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (872035-09-1) → (2S,5S,11bR,1'S)-2-[(Nα-(tert-butoxycarbonyl)-L-tryptophyl)amino]-5-[(1'-carbamoyl-2'-phenyl)ethyl]carbamoyl-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 48h;

DOI:10.1021/jm050689o

upstream raw materials:

Boc-Trp-OH

(S)-2-[((2S,5S,11bR)-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

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