(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid
• CAS No.: 185146-84-3
• Molecular Formula: C14H18N2O6
• Molecular Weight: 310.307
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50939932
• Wikidata: Q72450173
• Mol file: 185146-84-3.mol

Synonyms:185146-84-3;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid;Boc-2-nitro-L-phenylalanine;Boc-L-2-Nitrophenylalanine;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(2-nitrophenyl)propanoic acid;L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-2-nitro-;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(2-nitrophenyl)propanoic acid;Boc-Phe(2-NO2)-OH;SCHEMBL648928;DTXSID50939932;BSHMNGMAJNWNBP-JTQLQIEISA-N;(S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoicacid;MFCD01317708;AKOS015836623;AKOS015907808;AM83439;DS-16847;Boc-2-nitro-L-phenylalanine, 98% (HPLC);CS-0154533;EN300-1071109;A812931;Boc-L-2-Nitrophenylalanine (Boc-L-Phe(2-NO2)-OH);N-[tert-Butoxy(hydroxy)methylidene]-2-nitrophenylalanine;(S)-2-(tert-butoxycarbonylamino)-3-(2-nitrophenyl)propanoic acid;(S)-2-(tert-butyloxycarbonylamino)-3-(2-nitrophenyl)propanoic acid;(2s)-2-{[(t-butoxy)carbonyl]amino}-3-(2-nitrophenyl)propanoic acid;(S)-2-(tert-butyloxycarbonylamino)-3-(2-nitrophenyl) propanoic acid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 2.45E-10mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 488 °C at 760 mmHg
• Flash Point: 248.934 °C
• PSA: 121.45000
• Density: 1.29 g/cm³
• LogP: 3.02930
• Storage Temp.: Store at R.T.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 310.11648630
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

98%min ^*data from raw suppliers

Boc-L-2-Nitrophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1[N+](=O)[O-])C(=O)O
• Uses: Boc-L-2-Nitrophenylalanine is a protected derivative of L-Phenylalanine (P319415), and is used in the photocleavage of polypeptide backbones. L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further converted into dopamine, norepinephrine, and epinephrine.

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic acid

There total 1 articles about (S)-2-((tert-Butoxycarbonyl)amino)-3-(2-nitrophenyl)propanoic 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: 51.0%

→ N-(tert-butoxycarbonyl)-2-nitro-L-phenylalanine (185146-84-3,478183-69-6) + Boc-Phe(p-NO2)-OH (33305-77-0)

Guidance literature:

With 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide; at 55 - 60 ℃; for 3h; Inert atmosphere; Sealed tube;

Reference yield: 89.0%

N-(tert-butoxycarbonyl)-2-nitro-L-phenylalanine (185146-84-3,478183-69-6) + methylamine hydrochloride (593-51-1) → C15H21N3O5

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1021/jacs.9b12782

Reference yield:

N-(tert-butoxycarbonyl)-2-nitro-L-phenylalanine (185146-84-3,478183-69-6) → C10H13N3O3

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / N,N-dimethyl-formamide / 20 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 10 h / 20 °C

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jacs.9b12782

Refernces