Reaktionsgleichung
F[C:2]1[C:14](F)=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6]CC(O)=O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC(C)C[C@@H](B1O[C@@H]2C[C@@H]3C[C@H]([C@]2(C)O1)C3(C)C)N.FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C>CN(C)C=O>[C:4]([NH2:6])(=[O:5])[C:3]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:2]=1Komponenten
Edukt 5
HCID 81531Diisopropylethylamine
HCID 84468Trifluoroacetate
HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate
HCID 44244714(R)-3-Methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butan-1-amine
HCID 59816243[(2,3-Difluorobenzoyl)amino]acetic acidProdukt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a solution of [(2,3-difluorobenzoyl)amino]acetic acid (0.205 g, 0.95 mmol) in dimethylformamide (10 mL) were added TBTU (0.337 g, 1.0 mmol) and (1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butan-1-amine as its trifluoroacetate salt (0.362 g, 0.95 mmol). The mixture was allowed to cool to 0° C. and DIEA (0.498 mL, 2.9 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with water (100 mL) and the product partitioned into DCM. The organic layer was dried over sodium sulfate and the solvent removed to give 2,3-difluoro-N-[2-({1R)-3-methyl-1-[(3aR,4R,6R,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}amino)-2-oxoethyl]benzamide.
Aufarbeitung
- temperatureto warm to room temperature
- customThe reaction was quenched with water (100 mL)
- customthe product partitioned into DCM
- dry with materialThe organic layer was dried over sodium sulfate
- customthe solvent removed
Quellen und Nachweise
- ORD-Eintrag
- ord-474a7b3a6cae4cc7a2fc1d8e651e0575
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08772536B2
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