(2S)-2-azaniumyl-4-phenylbutanoate

Base Information

• Chemical Name: (2S)-2-azaniumyl-4-phenylbutanoate
• CAS No.: 943-73-7
• Molecular Formula: C10H13NO2
• Molecular Weight: 179.219
• Hs Code.: 2922.49
• Mol file: 943-73-7.mol

Synonyms:L-hph

Chemical Property of (2S)-2-azaniumyl-4-phenylbutanoate

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 9.79E-05mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 44 ° (C=1, 3mol/L HCl)
• Boiling Point: 324.8 °C at 760 mmHg
• PKA: 2.32±0.10(Predicted)
• Flash Point: 150.2 °C
• PSA: 63.32000
• Density: 1.164 g/cm³
• LogP: 1.73140
• Storage Temp.: Store at RT.
• Solubility.: Soluble in dilute aqueous acid.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 159

Purity/Quality:

99% ^*data from raw suppliers

L-Homophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@@H](C(=O)[O-])[NH3+]
• Description: L-Homophenylalanine is an amino acid derivative. It has been extensively used in the pharmaceutical industry as a precursor for production of angiotensin-converting enzyme (ACE) inhibitor: enalapril, delapril, quinapril and ramipril, which possesses significant clinical application in the management of hypertension and congestive heart failure (CHF). It acts as an anti-tumor reagent.
• Uses: L-Homophenylalanine is used as a precursor in the pharmaceutical industry for the production of angiotensin-converting enzyme (ACE) and R-(-)-Homophenylalanin-ethylester. It is also involved in the synthesis of NEPA [(S,S)-N-(1-Ethoxycarbonyl-3-phenylpropyl)alanine], which is a key intermediate to prepare the ACE-inhibitors: enalapril, delapril, quinapril and ramipril. It acts as an anti-tumor reagent.

Technology Process of (2S)-2-azaniumyl-4-phenylbutanoate

There total 81 articles about (2S)-2-azaniumyl-4-phenylbutanoate 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%

2-oxo-4-phenylbutyric acid (710-11-2) → D-homophenylalanine (943-73-7)

Guidance literature:

With formate dehydrogenase; NAD; ammonium formate; at 30 ℃; for 24h; PheDH;

DOI:10.1021/jo00308a012

Reference yield: 92.0%

(S)-2-Azido-4-phenyl-butyric acid (139040-47-4) → D-homophenylalanine (943-73-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 13h; under 760 Torr;

DOI:10.1021/ja00031a069

Reference yield: 91.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-oxo-2'-phenylethyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-57-2) → D-homophenylalanine (943-73-7) + D-homophenylalanine (82795-51-5)

Guidance literature:

With hydrogen; palladium dichloride; In tetrahydrofuran; ethanol; for 34h; under 2068.6 Torr; Yields of byproduct given;

DOI:10.1021/ja00213a031

upstream raw materials:

(R)-2-Acetamido-4-phenylbutansaeure

1-styrenyloxytrimethylsilane

(5S,6R)-3-Bromo-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

2-oxo-4-phenylbutyric acid

Downstream raw materials:

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

methyl 2S-2-amino-4-phenylbutanoate

(S)-2-benzoylamino-4-phenylbutyric acid

2-oxo-4-phenylbutanoic acid ethyl ester

Refernces

• 1、 Ahmad,Low,Shukor, S.R. Abd. "Immobilization of phenylalanine dehydrogenase onto Eupergit CM for the synthesis of (S)-2-amino-4-phenylbutyric acid". . p. 26 - 31. Retrieved 2013.
• 2、 Liu, Yayun,Meng, Lijun,Wu, Jianping,Yang, Lirong,Yin, Xinjian,Zhou, Haisheng. "Semi-rational hinge engineering: modulating the conformational transformation of glutamate dehydrogenase for enhanced reductive amination activity towards non-natural substrates". . p. 3376 - 3386. Retrieved 2020/06/09.
• 3、 Zhou, Haisheng,Meng, Lijun,Yin, Xinjian,Liu, Yayun,Xu, Gang,Wu, Jianping,Wu, Mianbin,Yang, Lirong. "Artificial Biocatalytic Cascade with Three Enzymes in One Pot for Asymmetric Synthesis of Chiral Unnatural Amino Acids". supporting information. p. 6470 - 6477. Retrieved 2019/11/02.