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Benzyl Bromide → HCID 68746130, Verbindung

HRID 333324
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333324
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1>CN(C=O)C.[Cl-].[Na+].O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH:9]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:12][CH2:34][C:31]2[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=2)=[O:11])=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 448910052-[(4-Bromophenyl)methyl]-3-[(tert-butoxycarbonyl)amino]propanoic acid

Produkt 1

HCID 68746130HCID 68746130, VerbindungAusbeute 7,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 57417360
Sodium chloride; water
Lösungsmittel

Versuchsvorschrift

A suspension of 3-(4-bromo-phenyl)-2-(tert-butoxycarbonylamino-methyl)-propionic acid (496 mg, 1.385 mmol), K2CO3 (383 mg, 2.77 mmol) and BnBr (0.493 ml, 4.15 mmol) in DMF (3 ml) was allowed to stir under nitrogen for 60 hours. The reaction mixture was cooled, and brine was added. The product was extracted with EtOAc, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50) and then purified by RP-HPLC (XBridge Prep Phenyl OBD, H2O (0.1% NH4OH)/CH3CN) to give benzyl 2-(4-bromobenzyl)-3-(tert-butoxycarbonylamino)propanoate (44 mg); Retention time=1.67 minutes (condition B); MS (ES+)=348.0 (m-Boc+2).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 50:50)
  8. custompurified by RP-HPLC (XBridge Prep Phenyl OBD, H2O (0.1% NH4OH)/CH3CN)

Quellen und Nachweise

ORD-Eintrag
ord-961a8c8010f9448a8efc1f7f2f70ed13
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877815B2

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