(alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine

Base Information

• Chemical Name: (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine
• CAS No.: 868540-16-3
• Molecular Formula: C31H42N4O6
• Molecular Weight: 566.698
• Mol file: 868540-16-3.mol

Synonyms:(alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine;(alphaS) - alpha - [(4 - acetyl Morpholine base) aMino] benzene ding acyl - L - bright aMMonia acyl - L - phenylalanine;L-Phenylalanine, (αS)-α-[[2-(4-Morpholinyl)acetyl]aMino]benzenebutanoyl-L-leucyl-;(alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzene;(S)-2-((S)-4-Methyl-2-((S)-2-(2-MorpholinoacetaMido)-4-phenylbutanaMido)pentanaMido)-3-phenylpropanoic acid;Carfilzomib intermidate

Chemical Property of (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine

Chemical Property:

• Boiling Point: 865.6±65.0 °C(Predicted)
• PKA: 3.50±0.10(Predicted)
• PSA: 137.07000
• Density: 1.190±0.06 g/cm3(Predicted)
• LogP: 2.88980
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-((S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-2-((S)-4-Methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenylpropanoic Acid is an intermediate for Carfilzomib (C183460), which is a second-generation proteasome inhibitor that is used as a treatment in relapsed and refractory multiple myeloma.

Technology Process of (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine

There total 23 articles about (alphaS)-alpha-[(4-Morpholinylacetyl)aMino]benzenebutanoyl-L-leucyl-L-phenylalanine 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:

C2HF3O2*C26H35N3O4 (868539-99-5) → (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid (868540-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / 0 - 20 °C

2: lithium hydroxide monohydrate / methanol / 3 h / 0 - 20 °C

With lithium hydroxide monohydrate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

DOI:10.1016/j.bmc.2019.07.044

Reference yield:

(S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido) pentanamido)-3-phenylpropanoate (875309-92-5) → (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid (868540-16-3)

Guidance literature:

With methanol; hydrogen; palladium 10% on activated carbon; In ethyl acetate; for 2h; under 760.051 Torr;

Reference yield:

C32H44N4O6 (1140908-89-9) → (S)-2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido)pentanamido)-3-phenyipropanoic acid (868540-16-3)

Guidance literature:

With lithium hydroxide; In methanol; water; at 0 - 5 ℃; for 12h;

upstream raw materials:

(S)-benzyl 2-((S)-4-methyl-2-((S)-2-(2-morpholinoacetamido)-4-phenylbutanamido) pentanamido)-3-phenylpropanoate

N-tert-butoxycarbonyl-L-leucine

methyl (2S)-2-amino-3-phenylpropanoate

(N-(tert-butoxycarbonyl)-L-leucinyl)-L-phenylalanine methyl ester

Downstream raw materials:

carfilzomib

Refernces

• 1、 Lei, Meng,Zhang, Haoyang,Miao, Hang,Du, Xiao,Zhou, Hui,Wang, Jia,Wang, Xueyuan,Feng, Huayun,Shi, Jingmiao,Liu, Zhaogang,Shen, Jian,Zhu, Yongqiang. "Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors". . p. 4151 - 4162. Retrieved 2019/08/07.
• 2、 -. "PROCESS FOR THE PREPARATION OF (2S)-N-((S)-1-((S)-4-METHYL-1-((R)-2-METHYL OXIRAN-2-YL)-1-OXOPENTAN-2-YLCARBAMOYL)-2-PHENYLETHYL)-2-((S)-2-(2-MORPHOLINO ACETAMIDO)-4-PHENYLBUTANAMIDO)-4-METHYLPENTANAMIDE". . . Retrieved 2016/11/14.