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Benzyl Bromide → Benzyl 3-[(tert-Butoxycarbonyl)aminomethyl]-5-Methyl-Hexanoate

HRID 1767293
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1767293
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:11][C:12]([O:14][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 16726400HCID 16726400, Verbindung

Produkt 1

HCID 21113527Benzyl 3-[(tert-Butoxycarbonyl)aminomethyl]-5-Methyl-HexanoateAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of (37) (1.24 g, 4.78 mmol) and Cs2CO3 (1.56 g, 4.78 mmol) in DMF (20 mL) was added benzyl bromide (0.56 mL, 4.68 mmol). The resulting mixture was stirred at ambient temperature until the reaction was complete (˜2 h, as monitored by LC/MS). The mixture was poured into ice water and extracted with dichloromethane. The combined organic phase was washed with water and brine, then dried over anhydrous Na2SO4. Filtration and removal of the solvent in vacuo afforded the title compound (38) (1.77 g, 100%), which was used without further purification in the following example. 1H-NMR (CDCl3, 400 MHz): δ 0.86 (2 d, 6H), 1.13 (m, 2H), 1.42 (s, 9H), 1.62 (m, 1H), 2.31 (m, 2H), 3.00 (m, 1H), 3.18 (m, 1H), 4.75 (br.s, 1H), 5.10 (s, 2H), 7.33 (m, 5H). MS (ESI) m/z 372.30 (M+Na+).

Aufarbeitung

  1. custom(˜2 h, as monitored by LC/MS)
  2. extractionextracted with dichloromethane
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationFiltration and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1ebf23bf37814dc588249d9a47cae433
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07232924B2

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