(R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Base Information

• Chemical Name: (R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid
• CAS No.: 65717-64-8
• Molecular Formula: C₁₈H₂₃N₃O₄
• Molecular Weight: 345.398
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID90426674
• Wikidata: Q72450297
• Mol file: 65717-64-8.mol

Synonyms:65717-64-8;N-Boc-1-phenylmethyl-D-histidine;(R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid;(2R)-3-(1-benzylimidazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;(2R)-2-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-3-[1-(phenylmethyl)-4-imidazolyl]propanoic acid;(2R)-3-(1-Benzyl-1H-Imidazol-4-Yl)-2-{[(Tert-Butoxy)Carbonyl]Amino}Propanoic Acid;SCHEMBL3429311;DTXSID90426674;D-Histidine,N-[(1,1-dimethylethoxy)carbonyl]-1-(phenylmethyl)-;MFCD00038628;AKOS015907641;AS-61205;1-Benzyl-N-(tert-butoxycarbonyl)-D-histidine;A835205;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[1-(phenylmethyl)imidazol-4-yl]propanoic acid

Chemical Property of (R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

Chemical Property:

• Vapor Pressure: 6.3E-14mmHg at 25°C
• Refractive Index: 1.572
• Boiling Point: 572.1 °C at 760 mmHg
• Flash Point: 299.8 °C
• PSA: 93.45000
• Density: 1.2 g/cm³
• LogP: 2.84270
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 345.16885622
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

98%min ^*data from raw suppliers

(R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CN(C=N1)CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CN(C=N1)CC2=CC=CC=C2)C(=O)O

Technology Process of (R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid

There total 1 articles about (R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)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:

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + Nim-benzyl-D-histidine (103772-40-3,31534-22-2) → N-(t-butoxycarbonyl)-im-benzyl-D-histidine (65717-64-8,81018-79-3)

Guidance literature:

DOI:10.1246/bcsj.58.172

Reference yield: 70.0%

D-alanine benzyl ester p-toluenesulphonate salt (41036-32-2) + N-(t-butoxycarbonyl)-im-benzyl-D-histidine (65717-64-8,81018-79-3) → Boc-D-His(Bzl)-D-Ala-OBzl (96523-69-2)

Guidance literature:

With N-ethylmorpholine;; 1-hydroxy-pyrrolidine-2,5-dione; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; 1.) -20 deg C, 1 h, 2.) 20 deg C;

DOI:10.3891/acta.chem.scand.38b-0647

Reference yield:

N-(t-butoxycarbonyl)-im-benzyl-D-histidine (65717-64-8,81018-79-3) → PhO-CH2CO-D-His(Bzl)-D-Ala (96523-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / N,N'-dicyclohexylcarbodiimide, N-ethylmorpholine, 1-hydroxybenzotriazole (or N-hydroxysuccinimide) / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 20 deg C

2: 50percent trifluoroacetic acid, anisole / CH₂Cl₂

3: 1.) 1-(4-chlorophenyl)-3-(4-methyl-1-piperazinyl)-2-propyn-1-one, 2.) N-ethylmorpholine / 1.) CH₂Cl₂, -10 deg C (1 h), room temperature (23 h), 2.) -10 deg C (1 h), room temperature (24 h)

4: 95 percent / H₂ / 10percent Pd/C / methanol / 760 Torr / Ambient temperature

With N-ethylmorpholine;; 1-hydroxy-pyrrolidine-2,5-dione; hydrogen; benzotriazol-1-ol; methoxybenzene; dicyclohexyl-carbodiimide; trifluoroacetic acid; 1-(4-chlorophenyl)-3-(4'-methyl-1'-piperazinyl)-2-propyn-1-one; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.3891/acta.chem.scand.38b-0647

upstream raw materials:

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine

N^im-benzyl-D-histidine

Downstream raw materials:

Boc-D-His(Bzl)-D-Ala-OBzl

D-His(Bzl)-D-Ala-OBzl

PhO-CH₂CO-D-His(Bzl)-D-Ala

PhO-CH₂CO-D-His(Bzl)-D-Ala-OBzl