L-4-Carbamoylphenylalanine

Base Information

• Chemical Name: L-4-Carbamoylphenylalanine
• CAS No.: 223593-04-2
• Molecular Formula: C₁₀H₁₂N₂O₃
• Molecular Weight: 208.217
• DSSTox Substance ID: DTXSID60376132
• Nikkaji Number: J3.567.417I
• Mol file: 223593-04-2.mol

Synonyms:L-4-Carbamoylphenylalanine;223593-04-2;(S)-2-Amino-3-(4-carbamoylphenyl)propanoic acid;(2S)-2-amino-3-(4-carbamoylphenyl)propanoic acid;L-4-Carbamoylphe;4-Carbamoylphenylalanine;SCHEMBL668747;(2S)-3-(4-aminocarbonylphenyl)-2-azanyl-propanoic acid;DTXSID60376132;MFCD01860658;AKOS015949714;PS-12792;CS-0205148;J3.567.417I;A878572;J-014666

Chemical Property of L-4-Carbamoylphenylalanine

Chemical Property:

• PSA: 106.41000
• LogP: 1.14050
• Storage Temp.: 2-8°C
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 208.08479225
• Heavy Atom Count: 15
• Complexity: 247

Purity/Quality:

97% ^*data from raw suppliers

L-4-Carbamoylphenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)C(=O)N
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)O)N)C(=O)N

Technology Process of L-4-Carbamoylphenylalanine

There total 2 articles about L-4-Carbamoylphenylalanine 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:

(S)-2-Benzyloxycarbonylamino-3-(4-carbamoyl-phenyl)-propionic acid benzyl ester (223593-01-9) → l-4-carbamoylphenylalanine (223593-04-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(99)00245-2

Reference yield:

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid (183070-42-0) → l-4-carbamoylphenylalanine (223593-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate, 1-hydroxybenzotriazole, diisopropylethylamine, NH₄Cl / dimethylformamide / 0.5 h / Ambient temperature

2: hydrogen / 10 percent Pd/C / methanol

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; ammonium chloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(99)00245-2

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + l-4-carbamoylphenylalanine (223593-04-2) → Fmoc-L-4-carbamoyl phenylalanine (204716-17-6)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; for 4h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(99)00245-2

upstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-(4-carbamoyl-phenyl)-propionic acid benzyl ester

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid

Downstream raw materials:

Fmoc-L-4-carbamoyl phenylalanine