Boc-trp-ome

Base Information

• Chemical Name: Boc-trp-ome
• CAS No.: 33900-28-6
• Molecular Formula: C₁₇H₂₂N₂O₄
• Molecular Weight: 318.373
• DSSTox Substance ID: DTXSID10427380
• Nikkaji Number: J1.249.147F
• Wikidata: Q82240036
• Mol file: 33900-28-6.mol

Synonyms:BOC-TRP-OME;33900-28-6;Boc-L-Trp-OMe;methyl (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;N-boc-l-tryptophan methyl ester;N-alpha-Boc-L-tryptophan Methyl Ester;(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(1H-indol-3-yl)propanoate;Boc-L-tryptophan methyl ester;MFCD01075094;SCHEMBL1486155;DTXSID10427380;QXLOVPXUZAOKBL-AWEZNQCLSA-N;L-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-, methyl ester;AC2361;NI+/--Boc-L-tryptophan methyl ester;AKOS015924233;AKOS016003101;CS-W022608;AS-17972;Methyl (tert-butoxycarbonyl)-L-tryptophanate;10.14272/QXLOVPXUZAOKBL-AWEZNQCLSA-N.1;doi:10.14272/QXLOVPXUZAOKBL-AWEZNQCLSA-N.1;(2S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester;(S)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid methyl ester

Chemical Property of Boc-trp-ome

Chemical Property:

• Melting Point: 139-140 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• Boiling Point: 505.7±45.0 °C(Predicted)
• PKA: 11.16±0.46(Predicted)
• PSA: 80.42000
• Density: 1.194±0.06 g/cm3(Predicted)
• LogP: 3.16760
• Storage Temp.: -15°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 318.15795719
• Heavy Atom Count: 23
• Complexity: 433

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-alpha-Boc-L-tryptophan methyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)OC
• Uses: Boc-Trp-OMe is a useful reagent for the preparation of trifluoroalkyl amines.

Technology Process of Boc-trp-ome

There total 30 articles about Boc-trp-ome 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (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) → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2003.04.005

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + L-tryptophan methyl ester (4299-70-1) → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6)

Guidance literature:

In tetrahydrofuran; at 25 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201400029

Reference yield: 99.0%

methanol (67-56-1) + Boc-Trp-OH (13139-14-5) → methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6)

Guidance literature:

With N-(methylpolystyrene)-4-(methylamino)pyridine; TEA; (2-chloro-1-pyridinio)-(Wang resin) triflate; In dichloromethane; for 1h;

DOI:10.1021/ol0480372

upstream raw materials:

indole

(S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester

Boc-Trp-OH

diazomethyl-trimethyl-silane

Downstream raw materials:

N-tert-butyloxycarbonyl-tryptophanal

(6S,13S)-4-ethyl-6,7,12,13-tetrahydro-14-(phenylmethyl)-6,13-imino-5H-pyrido[3',4':5,6]cyclooct[1,2-b]indole

(S)-methyl 2-[2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanamido]acetate

N-tert-butoxycarbonyl-1-[2-(triphenylsilyl)ethoxycarbonyl]-L-tryptophan methyl ester

Refernces

• 1、 Abas, Hossay,Mas-Roselló, Josep,Amer, Mostafa Mahmoud,Durand, Derek J.,Groleau, Robin R.,Fey, Natalie,Clayden, Jonathan. "Asymmetric and Geometry-Selective α-Alkenylation of α-Amino Acids". supporting information. p. 2418 - 2422. Retrieved 2019/02/09.
• 2、 Kondaparla, Srinivasarao,Debnath, Utsab,Dola, Vasantha Rao,Sinha, Manish,Katti, Seturam B.,Soni, Awakash,Srivastava, Kumkum,Puri, Sunil K.. "Synthesis, biological evaluation, and molecular modeling studies of chiral chloroquine analogues as antimalarial agents". . . Retrieved 2019/01/05.