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

Phenylacetic Acid → HCID 67333180, Verbindung

HRID 1672255
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1672255
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.[C:22]([O:26][C:27](=[O:54])[CH:28]([NH:38][C:39]([C:41]1[CH:46]=[CH:45][C:44]([C:47]2[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=2)=[CH:43][CH:42]=1)=[O:40])[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:25])([CH3:24])[CH3:23].CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:22]([O:26][C:27](=[O:54])[CH:28]([NH:38][C:39]([C:41]1[CH:42]=[CH:43][C:44]([C:47]2[CH:48]=[CH:49][C:50]([NH:53][C:8](=[O:10])[CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:51][CH:52]=2)=[CH:45][CH:46]=1)=[O:40])[CH2:29][CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([CH3:23])([CH3:24])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 999Phenylacetic AcidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 67333061HCID 67333061, Verbindung

Produkt 1

HCID 67333180HCID 67333180, VerbindungAusbeute 12,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14284
4-(Dimethylamino)pyridine
Katalysator
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of phenylacetic acid (89 mg, 0.65 mmol, 1 equiv) in DMF (10 mL) was added to EDCI (188 mg, 0.98 mmol, 1.5 equiv.). After stirring for 20 min, 2-[(4′-Amino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester (297 mg, 0.65 mmol, 1 equiv.) was added, followed by the addition of Et3N (0.23 mL, 1.64 mmol, 2.5 equiv.) and DMAP (16 mg, 0.13 mmol, 20%). The reaction mixture was allowed to stir at room temperature overnight. Reaction was complete as determined by TLC. DMF was removed and the residue was dissolved in EtOAc. The organic layer was washed with H2O and brine, and then dried over MgSO4. After solvent was evaporated, the crude residue was purified by HPLC to give 45 mg of 2-[(4′-Phenylacetylamino-biphenyl-4-carbonyl)-amino]-pentanedioic acid di-tert-butyl ester in 12% yield. MS (ESI) m/z 573.

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. customReaction
  3. customDMF was removed
  4. dissolutionthe residue was dissolved in EtOAc
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. customAfter solvent was evaporated
  8. customthe crude residue was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-0ae9ba0885aa400aa952dd9dc6cdbe50
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07998965B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion