N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide

Base Information

• Chemical Name: N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide
• CAS No.: 162358-09-0
• Molecular Formula: C25H39NO5
• Molecular Weight: 433.588
• Hs Code.: 2924299090
• UNII: 9JYX2M778X
• DSSTox Substance ID: DTXSID50442936
• Wikidata: Q72443996
• Mol file: 162358-09-0.mol

Synonyms:162358-09-0;N-[1,1-BIS[(ACETYLOXY)METHYL]-3-(4-OCTYLPHENYL)PROPYL]ACETAMIDE;2-Acetamido-2-(4-octylphenethyl)propane-1,3-diyl diacetate;Acetamide, N-[1,1-bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]-;[2-acetamido-2-(acetyloxymethyl)-4-(4-octylphenyl)butyl] Acetate;2-acetamido-2-(4-octylphenethyl)-propane-1,3-diyl diacetate;9JYX2M778X;SCHEMBL4917300;DTXSID50442936;AMY22206;BCP14873;Acetamide, N-[1,1-bis[(acetyloxy);AKOS016003565;AC-25900;CS-0166483;FT-0663175;A882962;FINGOLIMOD HYDROCHLORIDE IMPURITY H [EP IMPURITY];2-Acetamido-2-(4-octylphenethyl)propane-1,3-diyldiacetate;2-acetamido-2-acetoxymethyl-4-(4-octylphenyl)butyl acetate;2-acetamido-2-[(acetyloxy)methyl]-4-(4-octylphenyl)butyl acetate;acetamide,n-(1,1-bis((acetyloxy)methyl)-3-(4-octylphenyl)propyl)-;2-Acetamido-2-(4-octylphenethyl)propane-1,3-diyl Diacetate (Fingolimod Impurity;2-Acetamido-2-[(acetyloxy)methyl]-4-(4-octylphenyl)butyl acetate (non-preferred name)

Chemical Property of N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide

Chemical Property:

• Boiling Point: 582.22 °C at 760 mmHg
• PKA: 14.68±0.46(Predicted)
• Flash Point: 305.916 °C
• PSA: 81.70000
• Density: 1.043g/cm³
• LogP: 4.91420
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 17
• Exact Mass: 433.28282334
• Heavy Atom Count: 31
• Complexity: 522

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1=CC=C(C=C1)CCC(COC(=O)C)(COC(=O)C)NC(=O)C
• Uses: N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide is derived from Diethyl 2-Acetamidomalonate (D443130), which is a versatile building block used for the synthesis of various pharmaceutical and biologically active compounds. It is an intermediate for the preparation of Novobiocin (N888500) analogues as potential heat shock protein 90 inhibitors.

Technology Process of N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide

There total 20 articles about N-[1,1-Bis[(acetyloxy)methyl]-3-(4-octylphenyl)propyl]acetamide 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: 95.0%

2-acetamido-2-[2-(4-octanoylphenyl)ethyl]propane-1,3-diol diacetate (249289-07-4) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 2h;

DOI:10.1039/c3ra40894a

Reference yield:

diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (162358-08-9) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

2: 8.25 g / pyridine / 16 h / 20 °C

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; 1: Reduction / 2: Acetylation;

DOI:10.1021/jm000173z

Reference yield:

acetic anhydride (108-24-7) + diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate (162358-08-9) → 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate (162358-09-0)

Guidance literature:

diethyl 2-acetamido-2-[2-(4-octylphenyl)ethyl]malonate; With calcium chloride; In water; isopropyl alcohol; at 0.2 - 0.3 ℃; for 0.00166667h;

With sodium tetrahydroborate; In water; isopropyl alcohol; at 0 - 0.5 ℃; for 0.005h;

acetic anhydride; With dmap; In dichloromethane; at 0.15 - 0.5 ℃; for 0.002h; Solvent; Reagent/catalyst; Temperature;

upstream raw materials:

acetic anhydride

N-(1-hydroxy-2-(hydroxymethyl)-4-(4-octylphenyl) butan-2-yl) acetamide

n-octanoic acid chloride

acetic acid phenethyl ester

Downstream raw materials:

acetic acid 2-acetoxymethyl-2-acetylamino-4-(3-bromo-4-octylphenyl)butyl ester

acetic acid 2-acetoxymethyl-2-acetylamino-4-(2-bromo-4-octylphenyl)butyl ester

C₂₅H₃₈⁽¹⁸⁾FNO₅

C₂₅H₃₈FNO₅

Refernces

• 1、 -. "A PROCESS FOR THE PREPARATION OF 2-AMINO-1,3-PROPANE DIOL COMPOUNDS AND SALTS THEREOF". Paragraph 0112. . Retrieved 2016/03/01.
• 2、 Kandagatla, Bhaskar,Prasada Raju, Vetukuri Venkata Naga Kali Vara,Kumar, Narayana Sravan,Reddy, Ganta Madhusudhan,Srinivas, Katkam,Iqbal, Javed,Bandichhor, Rakeshwar,Oruganti, Srinivas. "Practical synthesis of fingolimod from diethyl acetamidomalonate". . p. 9687 - 9689. Retrieved 2013/09/02.