N-[(2-methylpropoxy)carbonyl]-beta-alanyltryptophylmethionyl-alpha-aspartylphenylalaninamide

Base Information

• Chemical Name: N-[(2-methylpropoxy)carbonyl]-beta-alanyltryptophylmethionyl-alpha-aspartylphenylalaninamide
• CAS No.: 77055-37-9
• Molecular Formula: C₃₇H₄₉N₇O₉S
• Molecular Weight: 767.904
• Mol file: 77055-37-9.mol

Synonyms:

Chemical Property of N-[(2-methylpropoxy)carbonyl]-beta-alanyltryptophylmethionyl-alpha-aspartylphenylalaninamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2-methylpropoxy)carbonyl]-beta-alanyltryptophylmethionyl-alpha-aspartylphenylalaninamide

There total 20 articles about N-[(2-methylpropoxy)carbonyl]-beta-alanyltryptophylmethionyl-alpha-aspartylphenylalaninamide 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: 86.0%

L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide hydrochloride (5609-49-4) + Boc-β-Ala-ONB (65785-41-3) → pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

With 4-methyl-morpholine; for 48h;

Reference yield: 24.0%

→ pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

Reference yield:

L-Phenylalanine amide (5241-58-7) → pentagastrin (5534-95-2,77055-37-9,7488-96-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) isobutyl chloroformate, N-methylmorpholine / 1.) DMF, 15 min, -18 deg C; 2.) 2 h, -10 - -20 deg C; 4 h, room temperature

2: 84 percent / H₂ / Pd black / methanol / 12 h

3: 80 percent / HONB, DCCI / dimethylformamide / 1.) 2 h, -20 deg C; 2.) 3 h, room temperature

4: 98 percent / HCl, CH₃COOH, C₂H₅SH / 0.75 h / Ambient temperature

5: 86 percent / N-methylmorpholine / 48 h

With 4-methyl-morpholine; hydrogenchloride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; (3aR,4R,7S,7aS)-2-hydroxy-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione (N-hydroxy-5-exo-norbornene-2,3-dicarboximide); ethanethiol; isobutyl chloroformate; palladium; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

L-Tryptophyl-L-methionyl-L-aspartyl-L-phenylalanine amide hydrochloride

Boc-β-Ala-ONB

Boc-βAla-Δ^ZTrp-Met-Asp-Phe-NH2

L-methionine

Refernces

• 1、 Hammadi, Akli,Lam, Hubert,Gondry, Muriel,Ménez, André,Genet, Roger. "Asymmetric reduction of (Z)-α,β-dehydrotryptophanyl-containing biological peptides with sulfur functionality. Influence of substrate on stereoselectivity". . p. 4473 - 4477. Retrieved 2007/10/03.
• 2、 -. "N-SUBSTITUTED CYCLOALKYL AND POLYCYCLOALKYL ALPHA-SUBSTITUTED TRP-PHE- AND PHENETHYLAMINE DERIVATIVES". . . Retrieved 2008/06/13.