Diisopropylethylamine → tert-butyl [(1S)-2-({5-[(2,5-dihydroxyphenyl)carbamoyl]isoxazol-3-yl}oxy)-1-methylethyl]carbamate

HRID 1026208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026208
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:20])[CH2:10][O:11][C:12]1[CH:16]=[C:15]([C:17]([OH:19])=O)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:22][C:23]1[CH:28]=[C:27]([OH:29])[CH:26]=[CH:25][C:24]=1[OH:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[OH:30][C:24]1[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:23]=1[NH:22][C:17]([C:15]1[O:14][N:13]=[C:12]([O:11][CH2:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH3:20])[CH:16]=1)=[O:19]

Komponenten

6

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 136850472-Aminobenzene-1,4-diol hydrochlorideHCID 677777153-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acid

Produkt 1

HCID 136372362tert-butyl [(1S)-2-({5-[(2,5-dihydroxyphenyl)carbamoyl]isoxazol-3-yl}oxy)-1-methylethyl]carbamateAusbeute 53,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)isoxazole-5-carboxylic acid (1.5 g), 2-aminobenzene-1,4-diol hydrochloride (0.847 g) and HATU (1.99 g) in DMF (20 mL) was added N,N-diisopropylethylamine (1.80 mL), and the mixture was stirred at room temperature for 5 hr. The solvent was evaporated under reduced pressure, 0.1M hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.11 g).

Aufarbeitung

  1. customThe solvent was evaporated under reduced pressure, 0.1M hydrochloric acid
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-afb404cb1a944c84b17135c235b5baf4
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729102B2

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