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

HRID 539594

Reaktionsgleichung

Reaktionsgleichung von HRID 539594
[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-d77bba02e4f74e2dae46d8cd23aae4c6
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871745B2

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