3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

Base Information

• Chemical Name: 3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
• CAS No.: 204716-17-6
• Molecular Formula: C25H22 N2 O5
• Molecular Weight: 430.46
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID70426011
• Mol file: 204716-17-6.mol

Synonyms:204716-17-6;3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid;3-(4-carbamoylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic Acid;(S)-Fmoc-L-4-carbamoylphenylalanine;SCHEMBL1054730;DTXSID70426011;(2S)-3-(4-carbamoylphenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid;MUNGLNMRFZUOTD-UHFFFAOYSA-N;FMOC-D,L-PHE(4-C(O)NH2);J-013344;3-(4-carbamoylphenyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoic acid

Chemical Property of 3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

Chemical Property:

• Boiling Point: 713.4±60.0 °C(Predicted)
• PKA: 3.69±0.10(Predicted)
• PSA: 118.72000
• Density: 1.336±0.06 g/cm3(Predicted)
• LogP: 4.41110
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 430.15287181
• Heavy Atom Count: 32
• Complexity: 668

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-L-4-carbamoylphenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)C(=O)N)C(=O)O

Technology Process of 3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid

There total 3 articles about 3-(4-Carbamoyl-phenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic 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:

4-((S)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-ethyl)-benzoic acid (183070-42-0) → Fmoc-L-4-carbamoyl phenylalanine (204716-17-6)

Guidance literature:

Multi-step reaction with 3 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

3: Na₂CO₃ / H₂O; dioxane / 4 h / Ambient temperature

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium carbonate; ammonium chloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

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

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-(4-carbamoyl-phenyl)-propionic acid benzyl ester (223593-01-9) → Fmoc-L-4-carbamoyl phenylalanine (204716-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / 10 percent Pd/C / methanol

2: Na₂CO₃ / H₂O; dioxane / 4 h / Ambient temperature

With hydrogen; sodium carbonate; palladium on activated charcoal; In 1,4-dioxane; methanol; water;

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:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

l-4-carbamoylphenylalanine

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

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

Downstream raw materials:

{1-(4-carbamoyl-benzyl)-2-oxo-2-[2-(4-phenyl-1H-imidazol-2-yl)-piperidin-1-yl]-ethyl}-carbamic acid 9H-fluoren-9-ylmethyl ester