(R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid

Base Information

• Chemical Name: (R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid
• CAS No.: 156130-68-6
• Molecular Formula: C16H23 N O4
• Molecular Weight: 293.363
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70426874
• Nikkaji Number: J3.115.318B
• Wikidata: Q72498833
• Mol file: 156130-68-6.mol

Synonyms:156130-68-6;(R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid;SCHEMBL2781406;DTXSID70426874;AKOS015911499;Boc-(R)-2-Amino-5-phenyl-pentanoic acid;CS-0433919;F79130;N-(tert-Butyloxycarbonyl)-5-phenyl-D-norvaline;(2R)-2-{[(tert-butoxy)carbonyl]amino}-5-phenylpentanoic acid;(2R)-2-[(1,1-dimethylethoxy)carbonyl]amino-5-phenylpentanoic acid;Benzenepentanoic acid, alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-, (alphaR)-

Chemical Property of (R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid

Chemical Property:

• PSA: 75.63000
• Density: 1.121
• LogP: 3.37810
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 293.16270821
• Heavy Atom Count: 21
• Complexity: 343

Purity/Quality:

98.0% ^*data from raw suppliers

(R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoicacid 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(CCCC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CCCC1=CC=CC=C1)C(=O)O

Technology Process of (R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid

There total 12 articles about (R)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic 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: 82.0%

C17H25NO2 → 2-(tert-butoxycarbonylamino)-5-phenyl-D-pentanoic acid (156130-68-6)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃;

DOI:10.1039/c5sc04984a

Reference yield:

1-Bromo-3-phenylpropane (637-59-2) → 2-(tert-butoxycarbonylamino)-5-phenyl-D-pentanoic acid (156130-68-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium ethoxide / ethanol / 1.5 h / 20 °C

1.2: 98 percent / ethanol / 16 h / Heating

2.1: NaOH / 3 h / 100 °C

3.1: 68.9 g / CoCl₂; KCl; KOH / acylase I from Aspergillus melleus / H₂O / 24 h / 40 °C / pH 8.0

4.1: 96 percent / hydrochloric acid / ethanol / 22 h / 85 °C

5.1: triethylamine / tetrahydrofuran / 18 h / 20 °C

6.1: 7.30 g / NaOH / 5 h / 60 °C

With hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium chloride; sodium ethanolate; triethylamine; acylase I from Aspergillus melleus; In tetrahydrofuran; ethanol; water;

DOI:10.1016/j.bmc.2005.07.070

Reference yield:

DL-N-acetyl-2-amino-5-phenylpentanoic acid (108019-30-3,5440-44-8) → 2-(tert-butoxycarbonylamino)-5-phenyl-D-pentanoic acid (156130-68-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 68.9 g / CoCl₂; KCl; KOH / acylase I from Aspergillus melleus / H₂O / 24 h / 40 °C / pH 8.0

2: 96 percent / hydrochloric acid / ethanol / 22 h / 85 °C

3: triethylamine / tetrahydrofuran / 18 h / 20 °C

4: 7.30 g / NaOH / 5 h / 60 °C

With hydrogenchloride; potassium hydroxide; sodium hydroxide; potassium chloride; triethylamine; acylase I from Aspergillus melleus; In tetrahydrofuran; ethanol; water;

DOI:10.1016/j.bmc.2005.07.070

upstream raw materials:

2-tert-butoxycarbonylamino-5-phenyl-pentanoic acid ethyl ester

1-Bromo-3-phenylpropane

DL-N-acetyl-2-amino-5-phenylpentanoic acid

2-acetylamino-2-(3-phenyl-propyl)malonic acid diethyl ester

Downstream raw materials:

[4-phenyl-1-(3-phenyl-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-butyl]-carbamic acid tert-butyl ester

[4-phenyl-1-(3-o-tolyl-8-aza-bicyclo[3.2.1]octane-8-carbonyl)-butyl]-carbamic acid tert-butyl ester

2-[8-(2-tert-butoxycarbonylamino-5-phenyl-pentanoyl)-8-aza-bicyclo[3.2.1]oct-3-yl]-benzoic acid ethyl ester

2-[(1R,3S,5S)-8-((R)-2-tert-Butoxycarbonylamino-5-phenyl-pentanoyl)-8-aza-bicyclo[3.2.1]oct-3-yl]-benzoic acid ethyl ester