Water → HCID 86729753, Verbindung

HRID 2272594Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272594
[NH2:1][CH2:2][CH:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)#[N:15].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>CN(C=O)C>[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:1][CH2:2][CH:3]([CH3:13])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:21])=[CH:18][CH:17]=1)#[N:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 120874-Cyanobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 44629801tert-Butyl (3-amino-2-methylpropyl)carbamate

Produkt 1

HCID 86729753HCID 86729753, VerbindungAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (3-amino-2-methylpropyl)carbamate (200 mg, 1.06 mmol), 4-cyanobenzoic acid (156 mg, 1.06 mmol), HATU (525 mg, 1.38 mmol) and TEA (0.444 mL, 3.19 mmol) in DMF (5 mL) was stirred at room temperature for 16 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane) to give tert-butyl (3-(4-cyanobenzamido)-2-methylpropyl)carbamate (311 mg, 0.980 mmol, 92%) as a white powder.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7ed7a29d768e484bb631a9c201ac4f76
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

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