Hydrochloric Acid → [(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid

HRID 1676101

Reaktionsgleichung

Reaktionsgleichung von HRID 1676101
[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([B:16]1[O:20][C@@H]2C[C@@H]3C[C@H]([C@]2(C)[O:17]1)C3(C)C)[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])=[O:5].Cl.B([O-])OCC(C)C>CO.CCCCCC>[Br:1][C:2]1[CH:32]=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:10][C@H:11]([B:16]([OH:20])[OH:17])[CH2:12][CH:13]([CH3:15])[CH3:14])=[O:9])=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 673667952-bromo-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamideHCID 178450000HCID 178450000, Verbindung

Produkt 1

HCID 25183866[(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acidAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21896459Hexane methanolLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-N-[2-({(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide (0.220 g, 0.44 mmol) in methanol/hexane (1:1) (2.2 mL) were added 1N HCl (1 mL, 1.0 mmol) and isobutyl boronate (0.078 g, 0.76 mmol). The reaction mixture was allowed to stir overnight. The reaction mixture was concentrated and purified by reverse phase HPLC to give [(1R)-1-({[(2-bromobenzoyl)amino]acetyl}amino)-3-methylbutyl]boronic acid (0.119 g, 73%).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d2c800ff803e446a9e73596805986261
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003819B2

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