Triethylsilane → 3-[(4-Hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carbox

HRID 1046447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1046447
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([I:27])=[CH:8][C:9]=1[N:10]([C:18]([CH:20]1[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]1)=[O:19])[CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][CH2:12]1)=[O:4].C[Si](C)(C)OC1CCOC1.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>[N+](C)([O-])=O.CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([I:27])=[CH:8][C:9]=1[N:10]([CH:11]1[CH2:12][CH2:13][CH:14]([OH:17])[CH2:15][CH2:16]1)[C:18]([CH:20]1[CH2:21][CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])=[O:4]

Komponenten

7

Edukt 4

HCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 581141515-Iodo-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl esterHCID 66849751Trimethyl-(tetrahydro-furan-3-yloxy)-silane

Produkt 1

HCID 249893473-[(4-Hydroxycyclohexyl)-(4-methylcyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carboxAusbeute 50,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6375NitromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of 5-iodo-3-[(4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester (2.5 g, 4.96 mmol) and FeCl3 (41 mg, 0.252 mmol) in nitromethane (15.0 mL) cooled to 0° C. was added neat trimethyl-(tetrahydro-furan-3-yloxy)-silane (955 mg, 5.95 mmol) followed by the dropwise addition of triethylsilane (0.947 mL, 5.92 mmol). The reaction was allowed to slowly warm to room temperature and stirred overnight. Sat. NaHCO3 was added and the reaction mixture was extracted with dichloromethane. The organic layer was washed with brine, dried over Na2SO4 and concentrated to give a solid. The crude solid was heated in methanol, cooled and collected by filtration to provide 3-[(4-hydroxy-cyclohexyl)-(4-methyl-cyclohexanecarbonyl)-amino]-5-iodo-thiophene-2-carboxylic acid methyl ester (1.27 g, 44%) as a colorless solid.

Aufarbeitung

  1. temperatureto slowly warm to room temperature
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a solid
  7. temperaturecooled
  8. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-272856e64a3b4111a1792c77d4fe2078
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08569302B2

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