Diisopropylethylamine → HCID 89852450, Verbindung

HRID 627128

Reaktionsgleichung

Reaktionsgleichung von HRID 627128
[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@H:21]([C:31]([OH:33])=O)[C:20]([CH3:34])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3].Cl.N.C[N:38](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:4][N:5]([C@H:18]1[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C@H:21]([C:31](=[O:33])[NH2:38])[C:20]([CH3:34])=[CH:19]1)[S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])(=[O:8])=[O:7])[CH:2]=[CH2:3]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12820921Azane;hydrochlorideHCID 89852049HCID 89852049, Verbindung2×

Produkt 1

HCID 89852450HCID 89852450, VerbindungAusbeute 70,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2S,5R)-5-(N-(allyloxy)-2-nitrophenylsulfonamido)-1-(tert-butoxycarbonyl)-3-methyl-1,2,5,6-tetrahydropyridine-2-carboxylic acid (Intermediate 82, 3.98 g, 8.00 mmol) in DMF (20 mL) at room temperature was added ammonia hydrochloride (0.856 g, 16.00 mmol), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (4.56 g, 12.00 mmol) and N-ethyl-N-isopropylpropan-2-amine (5.57 mL, 32.00 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate and washed with saturated sodium bicarbonate and three times with 1:1 brine:water. The organics were dried over magnesium sulfate, filtered and concentrated. The crude product was purified with silica gel chromatography (220 g, 10%-80% ethyl acetate/hexanes) to yield the desired product (2.79 g, 70.2%) as an yellow foam.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate and three times with 1:1 brine
  2. dry with materialThe organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified with silica gel chromatography (220 g, 10%-80% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-cf6182415be442a79d068ff2f230b0cd
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

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