162358-08-9

Basic information

• Product Name: diethyl 2-acetamido-2-(4-octylphenethyl)malonate
• Synonyms: diethyl 2-acetamido-2-(4-octylphenethyl)malonate;Propanedioic acid,2-(acetylamino)-2-[2-(4-octylphenyl)ethyl]-, 1,3-diethyl ester;Diethyl 2-(acetamido)-2-(2-(4-octylphenyl)ethyl)propanedioate;2-(AcetylaMino)-2-[2-(4-octylphenyl)ethyl]propanedioic Acid 1,3-Diethyl Ester;FingoliMod IMpurity 3;Fingolimod Imp.3;diethyl 2-acetamido-2-(4-octylphenethyl)malote;Propanedioic acid, (acetylamino)[2-(4-octylphenyl)ethyl]-, diethyl ester
• CAS NO: 162358-08-9
• Molecular Formula: C₂₅H₃₉NO₅
• Molecular Weight: 433.58086
• EINECS: 1592732-453-0
• Product Categories: Aromatics
• Mol File: 162358-08-9.mol

Chemical Properties

• Melting Point: 57-58°C
• Boiling Point: 570.727 °C at 760 mmHg
• Flash Point: 298.965 °C
• Appearance: White Solid
• Density: 1.043
• Storage Temp.: 2-8°C
• PKA: 12.17±0.46(Predicted)
• CAS DataBase Reference: diethyl 2-acetamido-2-(4-octylphenethyl)malonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl 2-acetamido-2-(4-octylphenethyl)malonate(162358-08-9)
• EPA Substance Registry System: diethyl 2-acetamido-2-(4-octylphenethyl)malonate(162358-08-9)

Safety Data

• Hazardous Substances Data: 162358-08-9(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

An impurity found in fingolimod (F805000).

InChI:InChI=1S/C25H39NO5/c1-5-8-9-10-11-12-13-21-14-16-22(17-15-21)18-19-25(26-20(4)27,23(28)30-6-2)24(29)31-7-3/h14-17H,5-13,18-19H2,1-4H3,(H,26,27)

Upstream product

• 99-73-0 para-bromophenacyl bromide 
• 629-05-0 n-octyne 
• 1068-90-2 2-acetylaminomalonic acid diethyl ester 
• 1187769-23-8 C₁₇H₂₀BrNO₆ 
• 219307-07-0 4'-(2-hydroxyethyl)octanophenone 
• 122-79-2 Phenyl acetate 
• 13433-00-6 diethyl aminomalonate hydrochloride 
• 1187769-24-9 C₂₅H₃₃NO₆ 
• 268557-53-5 diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl)propane-1,3-dioate 
• 268557-54-6 1-(2-bromoethyl)-4-octylbenzene 
• 162358-03-4 2-(4-octanoylphenyl)ethyl acetate 
• 103-45-7 acetic acid phenethyl ester 
• 111-64-8 n-octanoic acid chloride 
• 712223-57-9 acetic acid 2-[4-(trifluoromethanesulfonyloxy)phenyl]ethyl ester 

Downstream Products

• 162358-09-0 2-acetamido-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol diacetate 
• 162359-55-9 fingolimod 
• 596820-22-3 [1-(bis-benzyloxy-phosphoryloxymethyl)-3-(4-octyl-phenyl)-propyl]-carbamic acid benzyl ester 
• 596820-26-7 [3-tert-butoxycarbonylamino-5-(4-octyl-phenyl)-pent-1-enyl]-phosphonic acid diethyl ester 
• 596820-20-1 2-benzyloxycarbonylamino-4-(4-octyl-phenyl)-butyric acid 
• 596820-35-8 4-tert-butoxycarbonylamino-6-(4-octyl-phenyl)-hexanoic acid methyl ester 
• 596820-21-2 [1-hydroxymethyl-3-(4-octyl-phenyl)-propyl]-carbamic acid benzyl ester 

Relevant articles and documents

A new efficient synthesis of the immunosuppressive agent FTY-720

A new efficient five-step synthesis of the immunosuppressive agent FTY- 720 is described.

A PROCESS FOR THE PREPARATION OF 2-AMINO-1,3-PROPANE DIOL COMPOUNDS AND SALTS THEREOF

The present disclosure relates to processes for the preparation of 2-amino-1,3-propane diol compounds and their hydrochloride salts. Particularly, the present disclosure relates to processes for synthesizing 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol and its hydrochloride salt 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride respectively. The said process is safe, commercially feasible for large-scale synthesis and has improved efficacy along with many other advantages. The present disclosure also relates to the novel polymorphs of 2-amino-1,3-propane diol compound and its hydrochloride salt, where in 2-amino-1,3-propane diol compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol, and its hydrochloride salt is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride.

FINGOLIMOD HYDROCHLORIDE PROCESS

A process for preparation of diethyl 2-acetamido-2-(4-octyl phenyl)ethyl malonate (III), a key intermediate of fingolimod hydrochloride comprising reaction of 2-(4- octylphenyl)ethyl iodide (IV) with diethyl acetamido malonate in presence of a base and an iodinating agent and in an organic solvent. The compound of formula (III) thus obtained provided fingolimod hydrochloride (la) having associated impurities below the regulatory limits.

PROCESS FOR PREPARATION OF FINGOLIMOD

The present invention provides a process for preparation of fingolimod, a compound of Formula I or a pharmaceutically acceptable salt thereof, free of regioisomeric impurity compound of Formula IA

Synthesis and evaluation of fluorinated fingolimod (FTY720) analogues for sphingosine-1-phosphate receptor molecular imaging by positron emission tomography

Sphingosine-1-phosphate (S1P) is a lysophospholipid that evokes a variety of biological responses via stimulation of a set of cognate G-protein coupled receptors (GPCRs): S1P1-S1P5. S1P and its receptors (S1PRs) play important roles in the immune, cardiovascular, and central nervous systems and have also been implicated in carcinogenesis. Recently, the S1P analogue Fingolimod (FTY720) has been approved for the treatment of patients with relapsing multiple sclerosis. This work presents the synthesis of various fluorinated structural analogues of FTY720, their in vitro and in vivo biological testing, and their development and application as [18F]radiotracers for the study of S1PR biodistribution and imaging in mice using small-animal positron emission tomography (PET).

PREPARATION OF FINGOLIMOD AND ITS SALTS

The present application provide processes for the preparation of fingolimod and its pharmaceutically acceptable salts, process for the purification of fingolimod hydrochloride and process for the preparation of amorphous fingolimod hydrochloride.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES

The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.

PROCESS FOR THE PREPARATION OF 2-AMINO-2- [2- (4-C3-C21-ALKYL-PHENYL)ETHYL] PROPANE-1, 3-DIOLS

The present invention relates to improved processes for the production of 2-amino-2-[2-(4- C2-20-alkyl-phenyl)ethyl]propane-1,3-diols, and to compounds for use therein.

Synthesis of the key intermediate, diethyl 2-acetylamino-2-(2-(4- octanoylphenyl)ethyl)propane-1,3-dioate, of the immunomodulatory agent FTY720 (fingolimod)

The key intermediate, diethyl 2-acetylamino-2-(2-(4-octanoylphenyl)ethyl) propane-1,3-dioate (13), for the immunomodulatory agent FTY720 (2: fingolimod) was synthesized via Michael addition of diethyl(acetylamino) malonate (6) to 4-octanoylstyrene (12).