Water → HCID 178448638, Verbindung

HRID 536763

Reaktionsgleichung

Reaktionsgleichung von HRID 536763
[CH2:1]([N:5]1[N:6]([CH3:28])[C:7]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1F)[CH2:2][CH2:3][CH3:4].[SH:29][CH2:30][C:31]([CH3:34])([OH:33])[CH3:32].CC(C)([O-])C.[K+].O>CC(N(C)C)=O>[CH2:1]([N:5]1[N:6]([CH3:28])[C:7]([C:24]([CH3:27])([CH3:25])[CH3:26])=[CH:8]/[C:9]/1=[N:10]\[C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:13]=1[S:29][CH2:30][C:31]([OH:33])([CH3:34])[CH3:32])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 962WaterHCID 133387172-Methyl-1-sulfanylpropan-2-olHCID 23665647Potassium tert-butoxideHCID 178448620HCID 178448620, Verbindung

Produkt 1

HCID 178448638HCID 178448638, VerbindungAusbeute 25,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of Example 81C (400 mg, 1 mmol), 1-mercapto-2-methylpropan-2-ol (213 mg, 2 mmol) and potassium tert-butoxide (225 mg, 2 mmol) in dimethylacetamide (10 mL) was heated at 100° C. for 12 hours. The mixture was then poured into water and extracted with ethyl acetate. The acetate layer was washed with brine, dried with MgSO4, filtered, and concentrated under reduced pressure. Purification by chromatography (SiO2, eluant: EtOAc-MeOH 9:1) afforded 125 mg of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 0.90 (t, J=7.3 Hz, 3H), 1.25 (s, 6H), 1.31-1.42 (m, 11H), 1.58-1.81 (m, 2H), 2.95 (s, 2H), 3.87 (s, 3H), 4.30-4.43 (m, 2H), 4.70 (s, 1H), 6.84 (s, 1H), 7.40-7.65 (m, 2H), 8.21 (d, J=2.0 Hz, 1H). MS (ESI+) m/z 486 (M+H)+. Anal. calculated for C24H34F3N3O2S: C, 59.36; H, 7.06; N, 8.65. Found: C, 59.27; H, 6.74; N, 8.40.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe acetate layer was washed with brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by chromatography (SiO2, eluant: EtOAc-MeOH 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ebe1ea5222a40f4aae55276dd13afbe
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859596B2

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