Diisopropylethylamine → HCID 24809791, Verbindung

HRID 1446305Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446305
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([OH:15])=O.[C:16]1([CH:22]2[CH2:26][CH2:25][NH:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:12][N:11]=[CH:10][C:9]=1[C:13]([N:24]1[CH2:25][CH2:26][CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23]1)=[O:15]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 31467433-PhenylpyrrolidineHCID 224942765-(2-Chlorophenyl)-1,2-oxazole-4-carboxylic acid

Produkt 1

HCID 24809791HCID 24809791, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-(2-chlorophenyl)-isoxazole-4-carboxylic acid (51.6 mg, 0.231 mmol), 3-phenylpyrrolidine (40 mg, 0.271 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (92.6 mg, 0.288 mmol) and diisopropylethylamine (49.7 mg, 0.384 mmol) were mixed in dimethylformamide (1.5 mL) and stirred at room temperature over night. Solvent was evaporated in vacuo (0.5-1.0 mL) and the residue was taken up in dichloromethane (1 mL), filtered and purified by normal-phase chromatography (20-50% EtOAc:petroleum ether). The combined fractions were partitioned between H2O/Acetic acid (pH 4) and ethyl acetate. The organic fractions were washed with H2O/brine and concentrated in vacuo to afford the title compound. HRMS (ESI, pos. ion) m/z calcd for C20H17ClN2O2: 352.0979, found 352.0980.

Aufarbeitung

  1. customSolvent was evaporated in vacuo (0.5-1.0 mL)
  2. filtrationfiltered
  3. custompurified by normal-phase chromatography (20-50% EtOAc:petroleum ether)
  4. customThe combined fractions were partitioned between H2O/Acetic acid (pH 4) and ethyl acetate
  5. washThe organic fractions were washed with H2O/brine
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-abb57a98bbfd4458acb1a712c8d9014b
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666888B2

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