Sodium hydride → Ethyl 8-(benzyloxy)-6-[(1,1-dioxido-1,2-thiazinan-2-yl)acetyl]-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

HRID 494128Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494128
[S:1]1(=[O:8])(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.[H-].[Na+].Br[CH2:12][C:13]([C:15]1[N:19]2[CH2:20][CH2:21][N:22]([CH3:25])[C:23](=[O:24])[C:18]2=[C:17]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]=1[C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:14]>CN(C=O)C>[CH2:27]([O:26][C:17]1[C:16]([C:34]([O:36][CH2:37][CH3:38])=[O:35])=[C:15]([C:13](=[O:14])[CH2:12][N:2]2[CH2:3][CH2:4][CH2:5][CH2:6][S:1]2(=[O:8])=[O:7])[N:19]2[CH2:20][CH2:21][N:22]([CH3:25])[C:23](=[O:24])[C:18]=12)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 3035081,4-ButanesultamHCID 86624799Ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Produkt 1

HCID 68865106Ethyl 8-(benzyloxy)-6-[(1,1-dioxido-1,2-thiazinan-2-yl)acetyl]-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A mixture of 1,2-thiazinane 1,1-dioxide (70 mg, 0.51 mmol) and sodium hydride (0.51 mmol) in anhydrous DMF (2 mL) was stirred at room temperature for 30 minutes. The mixture was treated with a solution of ethyl 6-(bromoacetyl)-8-(benzyloxy)-2-methyl-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-7-carboxylate (0.23 g, 0.51 mmol) in DMF. The reaction mixture was stirred at room temperature overnight and concentrated under vacuum. The residue was partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 20 to 100% ethyl acetate in hexane gradient to afford the title compound.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationconcentrated under vacuum
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f5fb18212dac439d8b65bfd8c6b386f8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538112B2

Notizen zur Reaktion

Wird geladen…