Diisopropylethylamine → 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

HRID 1676097

Reaktionsgleichung

Reaktionsgleichung von HRID 1676097
[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([OH:10])=O)=[O:5].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:38][CH:39]([CH3:56])[CH2:40][C@@H:41]([B:43]1[O:47][C@@H:46]2[CH2:48][C@@H:49]3[CH2:52][C@H:51]([C@:45]2([CH3:55])[O:44]1)[C:50]3([CH3:54])[CH3:53])[NH2:42].FC(F)(F)C([O-])=O.CCN(C(C)C)C(C)C>CN(C)C=O>[F:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([NH:6][CH2:7][C:8]([NH:42][C@H:41]([B:43]1[O:47][C@H:46]2[CH2:48][C@H:49]3[CH2:52][C@@H:51]([C@@:45]2([CH3:55])[O:44]1)[C:50]3([CH3:53])[CH3:54])[CH2:40][CH:39]([CH3:56])[CH3:38])=[O:10])=[O:5]

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 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-amineHCID 59816243[(2,3-Difluorobenzoyl)amino]acetic acid

Produkt 1

HCID 673690412,3-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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

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

  1. temperatureto warm to room temperature
  2. customThe reaction was quenched with water (100 mL)
  3. customthe product partitioned into DCM
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed

Quellen und Nachweise

ORD-Eintrag
ord-911ac745d38b4b0a9af93277966ee8f3
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08003819B2

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