Diisopropylethylamine → HCID 67304072, Verbindung

HRID 61429

Reaktionsgleichung

Reaktionsgleichung von HRID 61429
[C:1]([O:5][C:6]([C@H:8]1[CH2:13][CH:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:11][NH:10][C@@H:9]1[C:19]([OH:21])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.[C:49]1([CH:55]2[CH2:59][CH2:58][NH:57][CH2:56]2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:18][O:17][C:15](=[O:16])[CH2:14][CH:12]1[CH2:11][NH:10][C@H:9]([C:19]([N:57]2[CH2:58][CH2:59][CH:55]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[CH2:56]2)=[O:21])[C@@H:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 31467433-PhenylpyrrolidineHCID 67304288(2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid

Produkt 1

HCID 67304072HCID 67304072, VerbindungAusbeute 104,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To an oven-dried 5 mL conical vial equipped with a magnetic stir bar and under a nitrogen gas atmosphere was placed sequentially: (2S,3S)-3-(tert-butoxycarbonyl)-5-(2-methoxy-2-oxoethyl)piperidine-2-carboxylic acid (50 mg, 0.166 mmol), anhydrous DMF (2 mL), BOP reagent (100 mg, 0.226 mmol), 3-phenyl-pyrrolidine (25 mg, 0.17 mmol), and N,N-diisopropyl ethylamine (0.086 mL, 0.49 mmol). After stirring the reaction mixture overnight, the reaction was quenched with 5% citric acid (1 mL) and the reaction mixture was diluted with ethyl acetate (15 mL) and water (4 mL). The aqueous layer was extracted with ethyl acetate (3×3 mL) and the combined organic phases were washed with saturated sodium bicarbonate (3×5 mL), brine (5 mL), dried (NaSO4), and concentrated in-vacuo to afford 75 mg of crude product that was used directly in the following hydrolysis. LCMS (ESI): 431 (M+H), 375 (M-t-Bu+2H+).

Aufarbeitung

  1. customTo an oven-dried 5 mL conical vial equipped with a magnetic stir bar and under a nitrogen gas atmosphere
  2. customthe reaction was quenched with 5% citric acid (1 mL)
  3. additionthe reaction mixture was diluted with ethyl acetate (15 mL) and water (4 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×3 mL)
  5. washthe combined organic phases were washed with saturated sodium bicarbonate (3×5 mL), brine (5 mL)
  6. dry with materialdried (NaSO4)
  7. concentrationconcentrated in-vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0ba1c173f229422fb8d454c486b6d35c
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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