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

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid
• CAS No.: 98628-27-4
• Molecular Formula: C16H23NO4
• Molecular Weight: 293.363
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40375926
• Nikkaji Number: J2.828.911A
• Wikidata: Q72509947
• Mol file: 98628-27-4.mol

Synonyms:98628-27-4;(S)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid;SCHEMBL1374859;(S)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoicacid;DTXSID40375926;AIFKBFKJMQTYAM-ZDUSSCGKSA-N;MFCD04117840;AKOS016844161;Benzenepentanoic acid, a-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-;DS-6167;Boc-(S)-2-Amino-5-phenyl-pentanoic acid;CS-0186159;N-(tert-Butoxycarbonyl)-5-phenyl-L-norvaline;C77368;A858520;(S)-2-(tert-butoxycarbonylamino)-5-phenylpentanoic acid;(S)-2-tert-butoxycarbonylamino-5-phenyl-pentanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-5-phenylpentanoic acid;(S)-2-((tert-Butoxycarbonyl)amino)-5-phenylpentanoic acid (Boc-L-Nva(Ph)-OH)

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

Chemical Property:

• Boiling Point: 480.2±45.0 °C(Predicted)
• PKA: 3.98±0.21(Predicted)
• PSA: 89.62000
• Density: 1.121
• LogP: 3.00430
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• 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%Min ^*data from raw suppliers

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

There total 4 articles about (S)-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:

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-4-phenylvaleric acid (62777-25-7,2046-19-7) → 2-tert-butoxycarbonylamino-5-phenyl-pentanoic acid (98628-27-4)

Guidance literature:

DOI:10.1016/S0040-4039(01)01790-7

Reference yield:

tert-butyl ((2R,3R)-1,2-dihydroxy-6-phenylhexan-3-yl)carbamate (1400695-38-6) → C17H25NO5 + 2-(tert-butoxycarbonylamino)-5-phenyl-D-pentanoic acid (156130-68-6) + 2-tert-butoxycarbonylamino-5-phenyl-pentanoic acid (98628-27-4)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; acetonitrile; at 20 ℃; for 24h; pH=6.8; Inert atmosphere;

DOI:10.1021/ol3021429

Reference yield:

[(2S,3S)-3-(3-Phenyl-propyl)-oxiranyl]-methanol → C17H25NO5 + 2-tert-butoxycarbonylamino-5-phenyl-pentanoic acid (98628-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: europium(III) trifluoromethanesulfonate; tetrabutylammoniun azide / tetrahydrofuran / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere

2.2: Inert atmosphere

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 24 h / 20 °C / pH 6.8 / Inert atmosphere

With sodium hypochlorite; sodium chlorite; lithium aluminium tetrahydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammoniun azide; europium(III) trifluoromethanesulfonate; In tetrahydrofuran; aq. phosphate buffer; acetonitrile;

DOI:10.1021/ol3021429

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-4-phenylvaleric acid

tert-butyl ((2R,3R)-1,2-dihydroxy-6-phenylhexan-3-yl)carbamate

C₁₂H₁₇N₃O₂

Downstream raw materials:

{1-[5-(3-methyl-1H-indazol-5-yl)-pyridin-3-yloxymethyl]-4-phenyl-butyl}-carbamic acid tert-butyl ester

[1-(5-bromo-pyridin-3-yloxymethyl)-4-phenyl-butyl]-carbamic acid tert-butyl ester

(S)-2-(2-(1H-imidazol-5-yl)acetamido)-N-(4-phenoxyphenyl)-5-phenylpentanamide

(S)-2-amino-N-(4-phenoxyphenyl)-5-phenylpentanamide

Refernces

• 1、 Catalano, John G,Deaton, David N,Furfine, Eric S,Hassell, Annie M,McFadyen, Robert B,Miller, Aaron B,Miller, Larry R,Shewchuk, Lisa M,Willard Jr., Derril H,Wright, Lois L. "Exploration of the P1 SAR of aldehyde cathepsin K inhibitors.". . p. 275 - 278. Retrieved 2007/10/03.