(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic acid

Base Information

• Chemical Name: (S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic acid
• CAS No.: 270596-42-4
• Molecular Formula: C15H20ClNO4
• Molecular Weight: 313.781
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID401147160
• Mol file: 270596-42-4.mol

Synonyms:270596-42-4;(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic acid;Boc-(S)-3-amino-4-(4-chloro-phenyl)-butyric acid;Boc-(S)-3-Amino-4-(4-chlorophenyl)butyric acid;(3S)-4-(4-chlorophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;(3S)-3-{[(tert-butoxy)carbonyl]amino}-4-(4-chlorophenyl)butanoic acid;Boc-(S)-3-amino-4-(4-chlorophenyl)-butyric acid;Boc-4-chloro-L-beta-homophenylalanine;(S)-4-Chloro-b-(Boc-amino)benzenebutanoic acid;SCHEMBL5966601;DTXSID401147160;AMY41863;(S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoicacid;MFCD01318372;AKOS015948823;CS-W009917;DS-6588;AC-22163;EN300-6472396;A877035;(S)-Boc-4-chloro-beta-Homophe-OH, >=98.0% (HPLC);(S)-3-(tert-butoxycarbonylamino)-4-(4-chlorophenyl)butanoic acid;(betaS)-4-Chloro-beta-[[(1,1-dimethylethoxy)carbonyl]amino]benzenebutanoic acid;(S)-N-(tert-Butoxycarbonyl)-3-amino-4-(4-chlorophenyl)butyric acid;(S)-3-(Boc-amino)-4-(4-chlorophenyl)butyric Acid

Chemical Property of (S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic acid

Chemical Property:

• Vapor Pressure: 1.23E-09mmHg at 25°C
• Refractive Index: 1.534
• Boiling Point: 470 °C at 760 mmHg
• PKA: 4.40±0.10(Predicted)
• Flash Point: 238 °C
• PSA: 75.63000
• Density: 1.22 g/cm³
• LogP: 3.64140
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 313.1080858
• Heavy Atom Count: 21
• Complexity: 359

Purity/Quality:

98%min ^*data from raw suppliers

Boc-4-chloro-L-beta-homophenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic acid

There total 11 articles about (S)-3-((tert-Butoxycarbonyl)amino)-4-(4-chlorophenyl)butanoic 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: 96.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-3-amino-4-(4-chlorophenyl)butanoic acid (270596-41-3,678969-20-5,678969-21-6) → (3S)-3-[[(tert-butoxy)carbonyl]amino]-4-(4-chlorophenyl)butanoic acid (270596-42-4,1824131-52-3)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 24h;

Reference yield: 40.0%

tert-butyl (S)-(1-(4-chlorophenyl)-4-diazo-3-oxobutan-2-yl)carbamate → (3S)-3-[[(tert-butoxy)carbonyl]amino]-4-(4-chlorophenyl)butanoic acid (270596-42-4,1824131-52-3)

Guidance literature:

With silver trifluoroacetate; triethylamine; In tetrahydrofuran; water; at -5 ℃; for 1h;

Reference yield:

Boc-p-chloro-L-Phe-OH (51301-86-1,57292-44-1,129101-26-4,68090-88-0) → (3S)-3-[[(tert-butoxy)carbonyl]amino]-4-(4-chlorophenyl)butanoic acid (270596-42-4,1824131-52-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; methyl chloroformate / tetrahydrofuran / 0.25 h / -10 °C

1.2: -30 - 20 °C

2.1: triethylamine; silver trifluoroacetate / tetrahydrofuran; water / 1 h / -5 °C

With silver trifluoroacetate; triethylamine; methyl chloroformate; In tetrahydrofuran; water;

upstream raw materials:

di-tert-butyl dicarbonate

(S)-3-amino-4-(4-chlorophenyl)butanoic acid

4-chlorophenylacetic Acid

5-[2-(4-chlorophenyl)-1-hydroxyethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Downstream raw materials:

(S)-tert-butyl 1-(4-chlorophenyl)-4-hydroxybutan-2-ylcarbamate

[1-(4-chloro-benzyl)-3-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester

C₂₈H₃₆ClN₃O₅S

Refernces

• 1、 -. "Synthesis method of chiral N-Boc-3-amino-4-aryl-butyric acid". Paragraph 0032; 0033; 0034; 0035; 0037; 0039. . Retrieved 2017/08/28.
• 2、 -. "SUBSTITUTED AMINO TRIAZOLES USEFUL AS HUMAN CHITINASE INHIBITORS". . . Retrieved 2017/03/21.