(2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]-3-phenylpropanoate

Base Information

• Chemical Name: (2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]-3-phenylpropanoate
• CAS No.: 3061-90-3
• Molecular Formula: C12H16 N2 O3
• Molecular Weight: 236.271
• Hs Code.: 2924299090
• Mol file: 3061-90-3.mol

Synonyms:

Chemical Property of (2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]-3-phenylpropanoate

Chemical Property:

• Appearance/Colour: White crystalline powder
• Refractive Index: 1.565
• Boiling Point: 487.6 °C at 760 mmHg
• PKA: 3.41±0.10(Predicted)
• Flash Point: 248.7 °C
• PSA: 92.42000
• Density: 1.222 g/cm³
• LogP: 1.23690
• Storage Temp.: −20°C
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 236.11609238
• Heavy Atom Count: 17
• Complexity: 269

Purity/Quality:

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

Ala-Phe-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)NC(CC1=CC=CC=C1)C(=O)[O-])[NH3+]
• Isomeric SMILES: C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)[O-])[NH3+]

Technology Process of (2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]-3-phenylpropanoate

There total 23 articles about (2S)-2-[[(2S)-2-azaniumylpropanoyl]amino]-3-phenylpropanoate 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%

N-benzyloxycarbonyl-L-alanyl-L-phenylalanine (2768-53-8) → L-alanyl-L-phenylalanine (3061-90-3)

Guidance literature:

With hydrogen; In methanol; at 27 ℃; for 2h; under 750.075 Torr; Reagent/catalyst; Green chemistry;

DOI:10.1039/c5ra02641e

Reference yield: 7.0%

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine (35661-39-3,136132-75-7) + N-Fmoc L-Phe (35661-40-6) → L-alanyl-L-phenylalanine (3061-90-3)

Guidance literature:

N-Fmoc L-Phe; With N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 1.08333h; Inert atmosphere;

With piperidine; In N,N-dimethyl-formamide; for 0.333333h;

N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; Further stages;

DOI:10.3762/BJOC.16.131

Reference yield:

pGlu-Lys-Ala-Phe-OH → L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + L-alanyl-L-phenylalanine (3061-90-3) + H-Lys-Ala-Phe-OH + H-Glu-Lys-Ala-Phe-OH

Guidance literature:

With hydrogenchloride; at 60 ℃; for 2h; Further Variations:; Reagents; other substrates; Product distribution;

DOI:10.1248/bpb.19.768

upstream raw materials:

L-phenylalanine

(S)-4-methyl-thiazolidine-2,5-dione

α-Alanyl-phenylalaninbenzylester

H-Ala-Phe-NH₂

Downstream raw materials:

L-alanin

L-phenylalanine

L-alanyl-L-alanyl-L-phenylalanine

N',N-bis(Boc)-N-guanidine Ala-Phe

Refernces

• 1、 Klepel, Florian,Ravoo, Bart Jan. "A dynamic combinatorial library for biomimetic recognition of dipeptides in water". supporting information. p. 1588 - 1595. Retrieved 2020/09/16.
• 2、 Ungaro, Vitor A.,Liria, Cleber W.,Romagna, Carolina D.,Costa, Natália J. S.,Philippot, Karine,Rossi, Liane M.,Machini, M. Teresa. "A green route for the synthesis of a bitter-taste dipeptide combining biocatalysis, heterogeneous metal catalysis and magnetic nanoparticles". . p. 36449 - 36455. Retrieved 2015/05/13.