Methyl n-(tert-butoxycarbonyl)valyltryptophanate

Base Information

• Chemical Name: Methyl n-(tert-butoxycarbonyl)valyltryptophanate
• CAS No.: 41863-58-5
• Molecular Formula: C22H31N3O5
• Molecular Weight: 417.4986
• NSC Number: 106697
• DSSTox Substance ID: DTXSID20295996
• Mol file: 41863-58-5.mol

Synonyms:41863-58-5;methyl n-(tert-butoxycarbonyl)valyltryptophanate;NSC106697;SCHEMBL11221428;DTXSID20295996;NSC-106697

Chemical Property of Methyl n-(tert-butoxycarbonyl)valyltryptophanate

Chemical Property:

• Vapor Pressure: 1.19E-15mmHg at 25°C
• Boiling Point: 627.3°Cat760mmHg
• Flash Point: 333.2°C
• Density: 1.173g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 417.22637110
• Heavy Atom Count: 30
• Complexity: 616

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)OC)NC(=O)OC(C)(C)C

Technology Process of Methyl n-(tert-butoxycarbonyl)valyltryptophanate

There total 5 articles about Methyl n-(tert-butoxycarbonyl)valyltryptophanate 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: 82.0%

(S)-methyl 2-(2,4-dinitrobenzenesulfonyl)-3-(1H-indol-3-yl)propanoate (930785-60-7) + (2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanethioic S-acid (187884-05-5) → methyl 2-(2-((t-butoxycarbonyl)amino)-3-methylbutanamido)-3-(indole-3yl)propanoate (41863-58-5)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/ol701583t

Reference yield: 76.0%

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) + (2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanethioic S-acid (187884-05-5) → methyl 2-(2-((t-butoxycarbonyl)amino)-3-methylbutanamido)-3-(indole-3yl)propanoate (41863-58-5)

Guidance literature:

(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanethioic S-acid; With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.0833333h;

(S)-tryptophan methyl ester hydrochloride; With 2,4-Dinitrofluorobenzene; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1002/anie.200805782

Reference yield: 75.0%

t-Boc-L-valine (13734-41-3) + L-tryptophan methyl ester hydrochloride → methyl 2-(2-((t-butoxycarbonyl)amino)-3-methylbutanamido)-3-(indole-3yl)propanoate (41863-58-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1039/d1cc01756j

upstream raw materials:

t-Boc-L-valine

L-tryptophan methyl ester

(S)-methyl 2-(2,4-dinitrobenzenesulfonyl)-3-(1H-indol-3-yl)propanoate

(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutanethioic S-acid