Ethanol → 7-[(1R)-2-Amino-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one, acetate salt

HRID 1689179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689179
[N:1]([CH2:4][C@@H:5]([C:7]1[C:15]2[S:14][C:13](=[O:16])[NH:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[OH:6])=[N+]=[N-].C([OH:20])C>[Pd]>[C:10]([OH:17])(=[O:20])[CH3:11].[NH2:1][CH2:4][C@@H:5]([C:7]1[C:15]2[S:14][C:13](=[O:16])[NH:12][C:11]=2[C:10]([OH:17])=[CH:9][CH:8]=1)[OH:6]

Komponenten

4

Edukt 2

HCID 702EthanolHCID 866367487-[(1R)-2-Azido-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one

Produkt 1

HCID 671669747-[(1R)-2-Amino-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one, acetate salt

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

5% Palladium on carbon type 87L paste (22 g) was added to 7-[(1R)-2-azido-1-hydroxy-ethyl]-4-hydroxy-3H-benzothiazol-2-one (example 1, step c) (225 g) dissolved in ethanol (3 L). The reaction was stirred under hydrogen (3 bar) for 48 h. A further 10 g of the catalyst was added and hydrogenation continued for a further 5 days. The reaction mixture was filtered and the solid (product+catalyst) suspended in ethanol (2.5 L) then acetic acid (150 mL) was added and the whole stirred overnight. The mixture was filtered again to remove the palladium on carbon catalyst. The solution was evaporated to dryness and azeotroped with toluene (2×1 L). The solid was slurried in tetrahydrofuran (1 L) for 4 hours, filtered and dried at 40° C. in vacuo to give the subtitled compound.

Aufarbeitung

  1. waithydrogenation continued for a further 5 days
  2. filtrationThe reaction mixture was filtered
  3. additionacetic acid (150 mL) was added
  4. stirringthe whole stirred overnight
  5. filtrationThe mixture was filtered again
  6. customto remove the palladium on carbon catalyst
  7. customThe solution was evaporated to dryness
  8. customazeotroped with toluene (2×1 L)
  9. waitThe solid was slurried in tetrahydrofuran (1 L) for 4 hours
  10. filtrationfiltered
  11. customdried at 40° C. in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5b278b5b829d46cabd1bb003835376a7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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