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

Base Information

• Chemical Name: N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine
• CAS No.: 900865-88-5
• Molecular Formula: C₂₆H₂₉N₃O₅
• Molecular Weight: 463.533
• Mol file: 900865-88-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine 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: 94.0%

(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) → N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine (900865-88-5)

Guidance literature:

With sodium hydroxide; In methanol; chloroform; at 0 ℃; for 1.16667h;

DOI:10.1016/j.bmc.2006.03.026 DOI:10.1016/j.tet.2007.04.045

Reference yield:

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid (66863-43-2) → N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine (900865-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HOBt; DCC / tetrahydrofuran / 18 h / 0 - 20 °C

2: 94 percent / NaOH / methanol; CHCl₃ / 1.17 h / 0 °C

With sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/j.tet.2007.04.045

Reference yield:

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine (900865-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / TFA / CH₂Cl₂; H₂O / 2 h / 20 °C

2: 76 percent / Et₃N / dimethylformamide / 104 h / 20 - 40 °C

3: 98 percent / HOBt; DCC / tetrahydrofuran / 18 h / 0 - 20 °C

4: 94 percent / NaOH / methanol; CHCl₃ / 1.17 h / 0 °C

With sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.04.045

upstream raw materials:

(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

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

L-Tryptophan

3-carboxy-1,2,3,4-tetrahydro-2-carboline

Downstream raw materials:

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