N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-(Z)lysine methyl ester

Base Information

• Chemical Name: N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-(Z)lysine methyl ester
• CAS No.: 900865-85-2
• Molecular Formula: C₃₂H₄₀N₄O₇
• Molecular Weight: 592.692
• Mol file: 900865-85-2.mol

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

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

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-(Z)lysine methyl ester

There total 4 articles about N-((3S)-2-N-Boc-1,2,3,4-tetrahydro-9H-β-carboline-3-carboxyl)-L-(Z)lysine 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: 90.0%

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride (27894-50-4) + (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-(Z)lysine methyl ester (900865-85-2)

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: 90.0%

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) + (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-(Z)lysine methyl ester (900865-85-2)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

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-(Z)lysine methyl ester (900865-85-2)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 90 percent / HOBt; DCC / tetrahydrofuran / 18 h / 0 - 20 °C

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

DOI:10.1016/j.tet.2007.04.045

upstream raw materials:

methyl (2S)-2-amino-6-{[(benzyloxy)carbonyl]amino}hexanoate hydrochloride

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

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

L-Tryptophan

Downstream raw materials:

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

(3S,12aS)-3-(4'-benzyloxycarbonylaminobutyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione

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