Octadecanedioic acid mono-tert-butyl ester

Bezeichnung:Octadecanedioic acid mono-tert-butyl ester

CAS-Nr843666-40-0

Englisch Name:Octadecanedioic acid mono-tert-butyl ester

CBNumberCB81519446

SummenformelC22H42O4

Molgewicht370.57

MOL-Datei843666-40-0.mol

Octadecanedioic acid mono-tert-butyl ester physikalisch-chemischer Eigenschaften

Schmelzpunkt	68 °C
Siedepunkt	470.7±18.0 °C(Predicted)
Dichte	0.950±0.06 g/cm3(Predicted)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
pka	4.78±0.10(Predicted)
Aggregatzustand	Solid
Farbe	White to Off-White
InChI	InChI=1S/C22H42O4/c1-22(2,3)26-21(25)19-17-15-13-11-9-7-5-4-6-8-10-12-14-16-18-20(23)24/h4-19H2,1-3H3,(H,23,24)
InChIKey	WDUQJXKBWRNMKI-UHFFFAOYSA-N
SMILES	C(OC(C)(C)C)(=O)CCCCCCCCCCCCCCCCC(O)=O

Sicherheit

HS Code

2917198090

Gefahreninformationscode (GHS)

Octadecanedioic acid mono-tert-butyl ester Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
Octadecanedioic acid mono-tert-butyl ester is a non-cleavable ADC linker or alkyl chain-based PROTAC linker for the synthesis of antibody-drug couplings (ADCs) and PROTACs.
Verwenden
18-(tert-Butoxy)-18-oxooctadecanoic Acid is a synthetic intermediate used in the preparation of semaglutide. It can be produced by the catalysis of 18-hydroxyoctadecanoic acid by ethyl bromoacetate in the presence of formamide and magnetic trifluoroacetic acid.
Verwenden
18-(tert-Butoxy)-18-oxooctadecanoic Acid is used to engineer long-acting, potent exendin-4 based GLP-1 analog for microstructure-based transdermal delivery for glycemic control.
Application
18-(tert-Butoxy)-18-oxooctadecanoic acid) is a short linker featuring a carboxylic acid and a tert-butyl ester. Carboxylic acids can be reacted with alcohols or amines, while the tert-butyl ester can be deprotected and further connected to another molecule. It is a pharmaceutical intermediate ingredient used in the preparation of somatostatin. It also has catalytic activity.
Synthese
A suspension of octadecanedioic Acid (15 g, 47.7 mmol) in Toluene (191 ml) was brought to reflux in 3 neck 1 L round bottom flask. When all the Acid was in solution, 1,1 -di-tert-butoxy-N, N-dimethylmethanamine (22.87 ml, 95 mmol) was added dropwise over 30 minutes. The reaction mixture was heated under reflux overnight. The reaction was stopped after 20 total hours of heating. The reaction mixture was cooled to room temperature, resulting in solid precipitation. The mixture was filtered by vacuum filtration. The resulting white solid was suspended in 200 ml dichloromethane and stirred for 15 minutes. The remaining solids were removed via vacuum filtration. The collected solids were again suspended in dichloromethane and stirred for 15 minutes. After a second filtration, the combined filtrates were concentrated in vacuo, and the resulting white powder 18-(tert-Butoxy)-18-oxooctadecanoic Acid was dried undervacuum.

Octadecanedioic acid mono-tert-butyl ester Upstream-Materialien And Downstream Produkte

Octadecanedioic acid mono-tert-butyl ester Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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