Boc-4-Amino-D-phenylalanine

Base Information

• Chemical Name: Boc-4-Amino-D-phenylalanine
• CAS No.: 164332-89-2
• Molecular Formula: C₁₄H₂₀N₂O₄
• Molecular Weight: 280.324
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID90427146
• Wikidata: Q72448331
• Mol file: 164332-89-2.mol

Synonyms:4-amino-N-(tert-butoxycarbonyl)-D-phenylalanine;(2R)-3-(4-Aminophenyl)-2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)propanoic acid;4-Amino-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine;D-Phenylalanine, 4-amino-N-[(1,1-dimethylethoxy)carbonyl]-;(2R)-3-(4-aminophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid;3-(4-aminophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;4-Amino-D-phenylalanine, N-BOC protected;

Chemical Property of Boc-4-Amino-D-phenylalanine

Chemical Property:

• Vapor Pressure: 3.25E-10mmHg at 25°C
• Melting Point: 130-132°C
• Refractive Index: 1.56
• Boiling Point: 484.9 °C at 760 mmHg
• PKA: 3.74±0.10(Predicted)
• Flash Point: 247 °C
• PSA: 101.65000
• Density: 1.213 g/cm³
• LogP: 2.76130
• Storage Temp.: -15°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 280.14230712
• Heavy Atom Count: 20
• Complexity: 344

Purity/Quality:

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

Boc-4-amino-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-4-Amino-D-phenylalanine

There total 15 articles about Boc-4-Amino-D-phenylalanine 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: 96.0%

Boc-Phe(p-NO2)-OH (33305-77-0) → L-N-tert-butoxycarbonyl-p-aminophenylalanine (55533-24-9,164332-89-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; Inert atmosphere;

DOI:10.1021/mp2001878

Reference yield: 80.0%

(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-nitrophenyl)propanoic acid (33305-77-0,86937-80-6,105453-25-6,61280-75-9) → (2R)-3-(4-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (55533-24-9,164332-89-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 24h; under 2585.74 Torr;

DOI:10.1016/j.ejmech.2006.03.021

Reference yield:

2-tert-butoxycarbonylamino-3-(4-nitro-phenyl)-propionic acid (86937-80-6) → L-N-tert-butoxycarbonyl-p-aminophenylalanine (55533-24-9,164332-89-2)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 2h; under 1810.07 Torr;

upstream raw materials:

Boc-Phe(p-NO₂)-OH

(S)-3-(4-azidophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid

L-phenylalanine

4-nitro-3-phenyl-L-alanine

Downstream raw materials:

(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]propanoic acid

Refernces

• 1、 Fatás, Paola,Bachl, Jürgen,Oehm, Stefan,Jiménez, Ana I.,Cativiela, Carlos,Díaz Díaz, David. "Multistimuli-responsive supramolecular organogels formed by low-molecular-weight peptides bearing side-chain azobenzene moieties". supporting information. p. 8861 - 8874. Retrieved 2013/07/26.
• 2、 Sassatelli, Mathieu,Debiton, éric,Aboab, Bettina,Prudhomme, Michelle,Moreau, Pascale. "Synthesis and?antiproliferative activities of?indolin-2-one?derivatives bearing amino acid moieties". . p. 709 - 716. Retrieved 2007/10/03.