Boc-Nalpha-methyl-DL-tryptophan

Base Information

• Chemical Name: Boc-Nalpha-methyl-DL-tryptophan
• CAS No.: 141408-33-5
• Molecular Formula: C17H22N2O4
• Molecular Weight: 318.36800
• Hs Code.: 2933990090
• European Community (EC) Number: 817-487-8
• Mol file: 141408-33-5.mol

Synonyms:Boc-Nalpha-methyl-DL-tryptophan;1452574-00-3;2-{[(tert-butoxy)carbonyl](methyl)amino}-3-(1H-indol-3-yl)propanoic acid;Boc-Nalpha-methyl-L-tryptophan;NA-(tert-butoxycarbonyl)-Na-methyltryptophan;3-(1H-indol-3-yl)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid;L-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-;starbld0011308;N-[(1,1-Dimethylethoxy)carbonyl]-N-methyl-L-tryptophan;N-Boc-N-methyl-DL-tryptophan;(2R)-2-{[(tert-butoxy)carbonyl](methyl)amino}-3-(1H-indol-3-yl)propanoic acid;N-Boc-N,1-dimethyl-D-tryptophan;CIC57400;AKOS015836763;EN300-1588006;J-007494

Chemical Property of Boc-Nalpha-methyl-DL-tryptophan

Chemical Property:

• PSA: 82.63000
• LogP: 3.03050
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 318.15795719
• Heavy Atom Count: 23
• Complexity: 446

Purity/Quality:

98%min ^*data from raw suppliers

Boc-Nα-methyl-L-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-Nalpha-methyl-DL-tryptophan

There total 1 articles about Boc-Nalpha-methyl-DL-tryptophan 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: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + L-abrine (526-31-8) → Nα-(tert-butoxycarbonyl)-Nα-methyl-L-tryptophan (141408-33-5,1452574-00-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 15h; Ambient temperature;

DOI:10.1021/jm970494j

Reference yield: 37.0%

H-Lys(CBz)-Asp(OBn)-Phe-NH2 hydrochloride (131450-40-3) + Nα-(tert-butoxycarbonyl)-Nα-methyl-L-tryptophan (141408-33-5,1452574-00-3) → Boc-(N-Me)Trp-Lys(CBz)-Asp(OBn)-Phe-NH2 (141408-80-2)

Guidance literature:

With 4-methyl-morpholine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; In dichloromethane; N,N-dimethyl-formamide; for 66h; Ambient temperature;

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) + Nα-(tert-butoxycarbonyl)-Nα-methyl-L-tryptophan (141408-33-5,1452574-00-3) → 1-(4-bromobenzyl)-Nα-(tert-butoxycarbonyl)-Nα-methyl-L-tryptophan

Guidance literature:

N^α-(tert-butoxycarbonyl)-N^α-methyl-L-tryptophan; With potassium hydroxide; In dimethyl sulfoxide; at 20 ℃; for 1h; Inert atmosphere;

1-bromomethyl-4-bromobenzene; In dimethyl sulfoxide; for 16h; Inert atmosphere;

upstream raw materials:

di-tert-butyl dicarbonate

L-abrine

Downstream raw materials:

Boc-(N-Me)Trp-Lys(CBz)-Asp(OBn)-Phe-NH₂

Boc-NMe-Trp-(NMe)Nle-Asp(OBzl)-Phe-NH₂

Boc-(N-Me)Trp-Lys-Asp-Phe-NH₂

Boc-(N-Me)Trp-Lys(CONH-Ph-o-Me)-Asp-Phe-NH₂

Refernces

• 1、 Levy, Daniel E.,Lapierre, France,Liang, Weisheng,Ye, Wenqing,Lange, Christopher W.,Li, Xiaoyuan,Grobelny, Damian,Casabonne, Marie,Tyrrell, David,Holme, Kevin,Nadzan, Alex,Galardy, Richard E.. "Matrix metalloproteinase inhibitors: A structure-activity study". . p. 199 - 223. Retrieved 2007/10/03.