(S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Base Information

• Chemical Name: (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
• CAS No.: 900865-72-7
• Molecular Formula: C₂₇H₃₁N₃O₅
• Molecular Weight: 477.56
• Mol file: 900865-72-7.mol

Synonyms:(S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Chemical Property of (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

There total 4 articles about (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate 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: 99.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (66863-43-2) → (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (900865-72-7)

Guidance literature:

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid; With benzotriazol-1-ol; In tetrahydrofuran; at 0 ℃; for 0.166667h;

methyl (2S)-2-amino-3-phenylpropanoate; With 4-methyl-morpholine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

DOI:10.1021/jm800249j

Reference yield: 98.0%

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) + (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (66863-43-2) → (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (900865-72-7)

Guidance literature:

With 4-methyl-morpholine; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; pH=8 - 9;

DOI:10.1016/j.bmc.2006.03.026

Reference yield:

3-carboxy-1,2,3,4-tetrahydro-2-carboline (42438-90-4) → (S)-tert-butyl 3-((S)-1-methoxy-1-oxo-3-phenylpropan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (900865-72-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / Et₃N / dimethylformamide / 104 h / 20 - 40 °C

2: 98 percent / HOBt; DCC / tetrahydrofuran / 18 h / 0 - 20 °C

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.04.045

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

methyl (2S)-2-amino-3-phenylpropanoate

L-Tryptophan

Downstream raw materials:

N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine

N-[(3S)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-phenylalanine

methyl (11aS)-1,2,3,5,11,11a-hexahydro-3,3-dimethyl-1-oxo-6H-imidazo[3',4':1,2]pyridin[3,4-b]indol-2-(2'S)-benzylacetate