Benzyl Bromide → N-(tert-Butoxycarbonyl)-3,4-dibenzyloxyphenylalanine benzyl ester

HRID 58900

Reaktionsgleichung

C([O-])([O-])=O.[K+].[K+].[C:7]([NH:14][C@@H:15]([CH2:19][C:20]1[CH:27]=[C:25]([OH:26])[C:23]([OH:24])=[CH:22][CH:21]=1)[C:16]([OH:18])=[O:17])([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(#N)C>[CH2:28]([O:26][C:25]1[CH:27]=[C:20]([CH2:19][C@H:15]([NH:14][C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C:16]([O:18][CH2:19][C:20]2[CH:27]=[CH:25][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:21]=[CH:22][C:23]=1[O:24][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

K2CO3 (21.0 g, 150 mmol) was added to a solution of Boc-L-dopa (10.0 g, 33 mmol) in acetonitrile (100 mL) followed by addition of benzyl bromide (21.0 g, 123 mmol). The suspension was heated at 50-60° C. for 4 h and then cooled to ambient temperature. The mixture was filtered and the filtration cake was washed with acetonitrile (50 mL). The filtrate and washings were combined and concentrated to dryness. The residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1) to afford (S)-benzyl 3-(3,4-bis(benzyloxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate (15.3 g, yield 80%).

Aufarbeitung

temperaturecooled to ambient temperature
filtrationThe mixture was filtered
washthe filtration cake was washed with acetonitrile (50 mL)
concentrationconcentrated to dryness
customThe residue was purified by flash column chromatography on silica gel (Hexane/EtOAc=20:1)

Quellen und Nachweise

ORD-Eintrag: ord-d81204e5ed364f4790ee10a56f8d230a
Quelldatensatz: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09434761B2

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