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Hydrogen Peroxide → 2-(R)-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butyric acid

HRID 1582043
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1582043
OO.C([C@@H]1COC(=O)N1[C:16](=[O:38])[C@H:17]([CH2:21][S:22]([N:25]1[CH2:30][CH2:29][C:28]2[C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[S:33][C:27]=2[CH2:26]1)(=[O:24])=[O:23])[CH:18]([CH3:20])[CH3:19])C1C=CC=CC=1.O.[OH-].[Li+].S([O-])([O-])=[O:43].[Na+].[Na+]>O1CCCC1.O>[CH2:26]1[C:27]2[S:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[C:28]=2[CH2:29][CH2:30][N:25]1[S:22]([CH2:21][C@H:17]([CH:18]([CH3:19])[CH3:20])[C:16]([OH:43])=[O:38])(=[O:23])=[O:24]
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Komponenten

7

Edukt 4

HCID 784Hydrogen PeroxideHCID 24437Sodium SulfiteHCID 168937Lithium hydroxide, monohydrateHCID 228882824(R)-Benzyl-3-[2-(R)-(3,4dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-one

Produkt 1

HCID 102703352-(R)-(3,4-Dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butyric acid
Ausbeute 87,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Hydrogen peroxide (30% aqueous, 0.15 ml) was added to a solution of 4-(R)-benzyl-3-[2-(R)-(3,4-dihydro-1H-benzo[4,5]thieno[2,3-c]pyridine-2-sulfonylmethyl)-3-methyl-butanoyl]-oxazolidin-2-one (180 mg) in tetrahydrofuran (5 ml) at 0° C., followed by a solution of lithium hydroxide monohydrate (30 mg) in water (3 ml). The reaction was stirred for 16 h, allowing to warm slowly to room temperature. A solution of sodium sulfite (200 mg) in water (5 ml) was added then the mixture was evaporated under reduced pressure. The aqueous residue was washed with diethyl ether (20 ml), acidified with citric acid and extracted with ethyl acetate (2×30 ml). The combined extracts were washed with brine (30 ml), dried (MgSO4), filtered and evaporated under reduced pressure to give the title compound (110 mg) in crude form.

Aufarbeitung

  1. customthe mixture was evaporated under reduced pressure
  2. washThe aqueous residue was washed with diethyl ether (20 ml)
  3. extractionextracted with ethyl acetate (2×30 ml)
  4. washThe combined extracts were washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-42b7ced74fa141eda7b4f776deb43089
Quelldatensatz
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06734189B2

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