Sodium Acetate → [(3R*,4S*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

HRID 420267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420267
[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([F:25])[CH:17]=2)[CH2:11]S[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[O:28][S:29]([O-:31])=O.[K+].CC([O-])=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:26])[NH:7][C@@H:8]1[C@@H:13]([OH:14])[C@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18]([F:25])[CH:17]=2)[CH2:11][S:29](=[O:31])(=[O:28])[CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Komponenten

7

Edukt 4

HCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 23707502Potassium hydroxy sulfiteHCID 68553360[(3R*,4R*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 131729359[(3R*,4S*,5S*)-5-(3-Fluoro-4-nitro-benzyl)-4-hydroxy-1,1-dioxo-hexahydro-1lambda*6*-thiopyran-3-yl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of [(3R*,4R*,5S*)-5-(3-fluoro-4-nitro-benzyl)-4-hydroxy-tetrahydro-thiopyran-3-yl]-carbamic acid tert-butyl ester (0.78 g, 2.0 mmol) in THF (15 mL) was added water (15 mL) and oxone (2.62 g, 4.2 mmol) and the reaction mixture was stirred for 2 h at 25° C. The excess oxone was destroyed after addition of 2 equivalents of NaOAc with sodium meta-bisulfite and the product was extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4 and evaporated. The title compound was obtained as a light yellow solid suitable for use in the next step: TLC (toluene-EtOAc 1:1) Rf=0.18; HPLC RtA=1.67 min; ESIMS [M+NH4]+=436; 1H NMR (600 MHz, DMSO-d6): δ 8.11 (t, 1H), 7.41 (d, 1H), 7.27 (d, 1H), 6.71 (d, 1H), 5.22 (d, 1H), 3.72 (m, 1H), 3.0-3.2 (m, 5H), 2.82 (s, 1H), 2.71 (dd, 1H), 2.17 (dd, 1H), 1.38 (s, 9H).

Aufarbeitung

  1. customThe excess oxone was destroyed
  2. extractionthe product was extracted with EtOAc
  3. washCombined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-a2d887294b414eca82c8a64a64251e82
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093406B2

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