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

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester

HRID 1177993
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1177993
CCN(C(C)C)C(C)C.[C:10]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH3:47][O:48][C:49](=[O:53])[CH2:50][NH:51][CH3:52]>CN(C=O)C.O>[CH3:47][O:48][C:49](=[O:53])[CH2:50][N:51]([C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)=[O:18])[CH3:52]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 66724(1,1'-Biphenyl)-4-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)

Produkt 1

HCID 43407419
[(Biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester
Ausbeute 77,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

DIPEA (880 mg, 1.2 mL, 6.8 mmol) was added to a stirred solution of biphenyl-4-carboxylic acid (300 mg, 1.5 mmol) in DMF (5 mL). HOBT (224 mg, 1.66 mmol) and EDCI (725 mg, 3.7 mmol) were then added at room temperature. After 2 minutes methylamino-acetic acid methyl ester hydrochloride salt (253 mg, 1.8 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and the product was extracted with EtOAc and the organic layer was washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to get the residue. The obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 20% EtOAc in hexane as eluent) filtered the solid precipitated out to afford 330 mg (76.96% yield) of [(biphenyl-4-carbonyl)-methyl-amino]-acetic acid methyl ester.

Aufarbeitung

  1. extractionthe product was extracted with EtOAc
  2. washthe organic layer was washed with brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto get the residue
  6. customThe obtained residue was purified by column chromatography (using silica gel of 60-120 mesh and 20% EtOAc in hexane as eluent)
  7. filtrationfiltered the solid
  8. customprecipitated out

Quellen und Nachweise

ORD-Eintrag
ord-938ce37734e54162b6f9dbe9ec40ac78
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842696B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion