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

Base Information

• Chemical Name: N-[(3S)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-phenylalanine
• CAS No.: 900866-05-9
• Molecular Formula: C₂₁H₂₁N₃O₃
• Molecular Weight: 363.416
• Mol file: 900866-05-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about N-[(3S)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-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: 95.0%

N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-phenylalanine (900865-88-5) → N-[(3S)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-phenylalanine (900866-05-9)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 0 ℃; for 1h;

DOI:10.1016/j.bmc.2006.03.026

Reference yield:

(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)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-phenylalanine (900866-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / NaOH / methanol; CHCl₃ / 1.17 h / 0 °C

2: 95 percent / HCl / ethyl acetate

With hydrogenchloride; sodium hydroxide; In methanol; chloroform; ethyl acetate;

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)-1,2,3,4-tetrahydro-β-carboline-3-carbonyl]-L-phenylalanine (900866-05-9)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 95 percent / HCl / ethyl acetate

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

DOI:10.1016/j.tet.2007.04.045

upstream raw materials:

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

(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