(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

Base Information

• Chemical Name: (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
• CAS No.: 305322-38-7
• Molecular Formula: C₃₄H₃₄N₄O₆
• Molecular Weight: 594.667
• Mol file: 305322-38-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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: 87.0%

methyl (3R)-3-amino-4-phenylbutanoate (190446-31-2) + (2R,5R,11bS)-2-(benzyloxycarbonyl)amino-5-carboxy-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole (305322-31-0) → (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 (305322-38-7)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In dichloromethane; at 20 ℃;

DOI:10.1021/jm000959x

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) → (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 (305322-38-7)

Guidance literature:

Multi-step reaction with 6 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

5: 96 percent / 2N NaOH / methanol / 18 h / 20 °C

6: 87 percent / BOP; TEA / CH₂Cl₂ / 20 °C

With sodium hydroxide; TEA; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; 10percent Pd/C; In methanol; dichloromethane; xylene;

DOI:10.1021/jm000959x

Reference yield:

2-amino-3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic 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 (305322-38-7)

Guidance literature:

Multi-step reaction with 3 steps

1: TEA / CH₂Cl₂ / 20 °C

2: 96 percent / 2N NaOH / methanol / 18 h / 20 °C

3: 87 percent / BOP; TEA / CH₂Cl₂ / 20 °C

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

DOI:10.1021/jm000959x

upstream raw materials:

methyl (3R)-3-amino-4-phenylbutanoate

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

(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