tert-Butyl carbonate → HCID 57907561, Verbindung

HRID 243661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 243661
[C:1](=[O:8])([O-])[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[Si:9]([O:16][C@H:17]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)[C@@H:18]1[NH:22][CH:21]([CH2:23][C:24]2[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>>[NH2:28][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][CH:21]2[CH2:20][CH2:19][C@H:18]([C@H:17]([O:16][Si:9]([C:12]([CH3:13])([CH3:15])[CH3:14])([CH3:10])[CH3:11])[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=3)[N:22]2[C:1]([O:2][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:8])=[CH:30][CH:29]=1

Komponenten

3

Edukt 2

HCID 4613278tert-Butyl carbonateHCID 57907535HCID 57907535, Verbindung2×

Produkt 1

HCID 57907561HCID 57907561, VerbindungAusbeute 78 %

Versuchsvorschrift

To a solution of 33 mg (0.07 mmol) of 4-({(5R)-5-[(R)-([tert-butyl(dimethyl)silyl]oxy}(3-chlorophenyl)methyl]pyrrolidin-2-yl}methyl)aniline in 1 mL of anhydrous THF (from Step A) was added tert-butyl carbonate (15.3 mg, 0.07 mmol), followed by TEA (13 uL, 0.07 mmol) and the resulting solution stirred at room temperature under nitrogen atmosphere overnight. The reaction mixture was put directly on a preparative plate (500 uM) and eluted with 30% ethyl acetate in hexane to afford the title compound (25 mg, 78%). m/z (ES) 530, 532 (M, M+2)+, 430, 432 (M-Boc, M-Boc+2)+.

Aufarbeitung

  1. washeluted with 30% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-70e631aae0e8405183da4242c2271d31
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653260B2

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