StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → {[2-(Tert-butoxycarbonyl-methyl-amino)acetyl]-methyl-amino}-acetic acid ethyl ester

HRID 73909
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 73909
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]([OH:13])=O)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.ClC(OCC(C)C)=O.Cl.[CH2:30]([O:32][C:33](=[O:37])[CH2:34][NH:35][CH3:36])[CH3:31]>C(Cl)Cl>[CH2:30]([O:32][C:33](=[O:37])[CH2:34][N:35]([C:11](=[O:13])[CH2:10][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH3:9])[CH3:36])[CH3:31]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 171173Ethyl N-methylaminoacetate hydrochloride

Produkt 1

HCID 57470192{[2-(Tert-butoxycarbonyl-methyl-amino)acetyl]-methyl-amino}-acetic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

To a stirred solution of (tert-butoxycarbonyl-methyl-amino)-acetic acid (37 g, 0.2 mol) and Et3N (60.6 g, 0.6 mol) in CH2Cl2 (300 mL) was added isobutyl chloroformate (27.3 g, 0.2 mmol) dropwise at −20° C. under argon. After stirring for 0.5 h, methylamino-acetic acid ethyl ester hydrochloride (30.5 g, 129 mmol) was added dropwise at −20° C. The mixture was allowed to warm to room temperature (c.a. 1 h) and quenched with water (500 mL). The organic layer was separated, washed with 10% citric acid solution, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (petroleum ether/EtOAc 1:1) to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid ethyl ester (12.5 g, 22

Aufarbeitung

  1. customquenched with water (500 mL)
  2. customThe organic layer was separated
  3. washwashed with 10% citric acid solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (petroleum ether/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4f98014265354558a01cdb1b0fffcff1
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829204B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion