2-Acetamido-4-phenylbutanoic acid

Base Information

• Chemical Name: 2-Acetamido-4-phenylbutanoic acid
• CAS No.: 5440-40-4
• Molecular Formula: C12H15 N O3
• Molecular Weight: 221.256
• Hs Code.: 2924299090
• NSC Number: 20162
• DSSTox Substance ID: DTXSID30281108
• Nikkaji Number: J1.856.940J
• Mol file: 5440-40-4.mol

Synonyms:2-acetamido-4-phenylbutanoic acid;60505-02-4;2-(acetylamino)-4-phenylbutanoic acid;5440-40-4;Benzenebutanoic acid, a-(acetylamino)-;NSC20162;Maybridge3_000392;SCHEMBL6931278;DTXSID30281108;CHEBI:167784;HMS1432B18;MFCD18862874;NSC-20162;AKOS013014221;SB79891;IDI1_011779;BS-17291;CS-0149808;FT-0640883;D83858;EN300-1217906;F2147-6633

Chemical Property of 2-Acetamido-4-phenylbutanoic acid

Chemical Property:

• Vapor Pressure: 2.68E-09mmHg at 25°C
• Boiling Point: 461.1°C at 760 mmHg
• Flash Point: 232.6°C
• PSA: 66.40000
• Density: 1.169g/cm³
• LogP: 1.59940
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 221.10519334
• Heavy Atom Count: 16
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

2-Acetamido-4-phenylbutanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC(CCC1=CC=CC=C1)C(=O)O

Technology Process of 2-Acetamido-4-phenylbutanoic acid

There total 22 articles about 2-Acetamido-4-phenylbutanoic acid 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: 89.5%

D,L-homophenylalanine (1012-05-1) + acetic anhydride (108-24-7) → 2-(acetylamino)-4-phenylbutanoic acid (5440-40-4)

Guidance literature:

With sodium hydroxide; In water; at 0 - 5 ℃; for 1h; pH=11 - 11.5;

DOI:10.1016/j.tetasy.2004.02.026

Reference yield: 51.0%

2-(acetylamino)-4-phenylbutanoic acid (5440-40-4) → D-homophenylalanine (943-73-7) + (2R)-N-acetyl-2-amino-4-phenylbutyric acid (5440-40-4,60505-02-4,96613-91-1,63393-59-9)

Guidance literature:

With L-aminoacylase; cobalt(II) chloride; In aq. buffer; at 20 - 38 ℃; for 1h; pH=7.5; enantioselective reaction; Inert atmosphere; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/acs.orglett.8b03910

Reference yield:

2-hydroxy-4-phenylbutanoic acid (4263-93-8,111611-91-7) → D-homophenylalanine (943-73-7) + (2R)-N-acetyl-2-amino-4-phenylbutyric acid (5440-40-4,60505-02-4,96613-91-1,63393-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium nitrite; 2-azatricyclo[3.3.1.1^3,7]decan-2-ol / water; acetonitrile; aq. phosphate buffer / 2 h / 20 °C / Inert atmosphere

2: phenylglycin / water; acetonitrile / 24 h / Inert atmosphere; Reflux

3: sodium hydroxide / water / 2 h / 20 °C / Inert atmosphere

4: L-aminoacylase; cobalt(II) chloride / aq. buffer / 1 h / 20 - 38 °C / pH 7.5 / Inert atmosphere; Resolution of racemate; Enzymatic reaction

With L-aminoacylase; 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; phenylglycin; cobalt(II) chloride; sodium hydroxide; sodium nitrite; In aq. phosphate buffer; water; acetonitrile;

DOI:10.1021/acs.orglett.8b03910

upstream raw materials:

D,L-homophenylalanine

2-acetylamino-2-phenylethylmalonic acid diethyl ester

acetic anhydride

5-phenylethyl-imidazolidine-2,4-dione

Downstream raw materials:

D-homophenylalanine

(2R)-N-acetyl-2-amino-4-phenylbutyric acid

p-tolylsulfonic caid salt of D-homophenylalanine benzyl ester

D-homophenylalanine

Refernces

• 1、 Chen, Lei,Du, Ding,Feng, Jie,Gao, Jian,Lu, Tao,Ma, Rui,Shi, Zhihao,Zhang, Kuili. "Bio- And Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis". supporting information. . Retrieved 2020/09/02.
• 2、 Vaidya, Bhalchandra K.,Kuwar, Suyog S.,Golegaonkar, Sandeep B.,Nene, Sanjay N.. "Preparation of cross-linked enzyme aggregates of l-aminoacylase via co-aggregation with polyethyleneimine". experimental part. p. 184 - 191. Retrieved 2012/03/22.