Sodium Carbonate → HCID 89923757, Verbindung

HRID 1752648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1752648
[OH:1][C@@H:2]([C:7]1[C:8]([I:18])=[C:9]2[CH:16]=[CH:15][N:14]([CH3:17])[C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4].C(O[C:23]([CH3:26])([CH3:25])[CH3:24])(=O)C.C([O-])([O-])=O.[Na+].[Na+]>>[C:23]([O:1][C@@H:2]([C:7]1[C:8]([I:18])=[C:9]2[CH:16]=[CH:15][N:14]([CH3:17])[C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4])([CH3:26])([CH3:25])[CH3:24]

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 10908tert-Butyl acetateHCID 89933754HCID 89933754, Verbindung

Produkt 1

HCID 89923757HCID 89923757, VerbindungAusbeute 72 %

Versuchsvorschrift

A solution of (S)-methyl 2-hydroxy-2-(4-iodo-1,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (9.6 g, 26.7 mmol) in tert-butyl acetate (349 ml, 2583 mmol) was treated dropwise with HClO4 (12.37 ml, 144 mmol). After 1 h, the reaction mixture was poured into 2M Na2CO3 and the layers partitioned. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified by ISCO (0-60% EtOAc-hexanes) to afford the title compound as a white foam (8.0 g, 71%). 1H NMR (CHLOROFORM-d) δ 7.13 (d, J=3.3 Hz, 1H), 6.30 (d, J=3.3 Hz, 1H), 5.75 (s, 1H), 3.84 (s, 3H), 3.67 (s, 3H), 2.73 (s, 3H), 1.25 (s, 9H). LC/MS (m/z) ES+=416.9 (M+1)+

Aufarbeitung

  1. customthe layers partitioned
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by ISCO (0-60% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eda028cd2a714ae59759903e37ed8833
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09163023B2

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