methyl N-(tert-butoxycarbonyl)tryptophylisoleucinate

Base Information

• Chemical Name: methyl N-(tert-butoxycarbonyl)tryptophylisoleucinate
• CAS No.: 72156-60-6
• Molecular Formula: C23H33 N3 O5
• Molecular Weight: 431.5252
• Mol file: 72156-60-6.mol

Synonyms:L-Isoleucine,N-[N-[(1,1-dimethylethoxy)carbonyl]-L-tryptophyl]-, methyl ester; NSC 262674

Chemical Property of methyl N-(tert-butoxycarbonyl)tryptophylisoleucinate

Chemical Property:

• Vapor Pressure: 3.83E-16mmHg at 25°C
• Boiling Point: 637.3°C at 760 mmHg
• Flash Point: 339.2°C
• Density: 1.159g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl N-(tert-butoxycarbonyl)tryptophylisoleucinate

There total 3 articles about methyl N-(tert-butoxycarbonyl)tryptophylisoleucinate 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: 99.0%

methyl L-isoleucinate hydrochloride (18598-74-8) + Boc-Trp-OH (13139-14-5) → N-tert-butoxycarbonyl-L-tryptophanyl-L-isoleucine methyl ester (72156-60-6)

Guidance literature:

With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 2.5h;

DOI:10.1002/(SICI)1522-2675(19991110)82:11<1899::AID-HLCA1899>3.0.CO;2-M

Reference yield: 98.0%

H2N-Ile-OMe*xHCl + Boc-Trp-OH (13139-14-5) → N-tert-butoxycarbonyl-L-tryptophanyl-L-isoleucine methyl ester (72156-60-6)

Guidance literature:

With endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In neat (no solvent); at 60 ℃; for 0.25h; Microwave irradiation; Green chemistry;

DOI:10.1039/c3ra46643d

Reference yield: 92.0%

L-isoleucine methyl ester (2577-46-0) + Boc-Trp-OH (13139-14-5) → N-tert-butoxycarbonyl-L-tryptophanyl-L-isoleucine methyl ester (72156-60-6)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jm050488k

upstream raw materials:

methyl L-isoleucinate hydrochloride

Boc-Trp-OH

L-isoleucine methyl ester

Downstream raw materials:

H₂N-Phg-Trp-Ile-OMe

Boc-Phg-Trp-Ile-OMe

Boc-Glu(OBzl)-Phg-Trp-Ile-OMe

N-tert-butoxycarbonyl-L-tryptophanyl-L-isoleucine methyl ester

Refernces

• 1、 Mahindra, Amit,Nooney, Karthik,Uraon, Shrikant,Sharma, Krishna K.,Jain, Rahul. "Microwave-assisted solution phase peptide synthesis in neat water". . p. 16810 - 16816. Retrieved 2013/09/23.
• 2、 Coste, Alexis,Toumi, Mathieu,Wright, Karen,Razafimahaleo, Vanessa,Couty, Francois,Marrot, Jerome,Evano, Gwilherm. "Copper-catalyzed cyclization of lodo-tryptophans: A straightforward synthesis of pyrroloindoles". supporting information; experimental part. p. 3841 - 3844. Retrieved 2009/07/01.