CID 66185 → 1-{[3-(Tert-butyl-dimethylsilanyloxy)-propyl]-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}cyclopentanecarboxylic acid benzyl ester

HRID 323798

Reaktionsgleichung

Reaktionsgleichung von HRID 323798
[CH2:1]([O:8][C:9]([C:11]1([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[K+].[C:44]([Si:48]([O:51][CH2:52][CH2:53][CH2:54]I)([CH3:50])[CH3:49])([CH3:47])([CH3:46])[CH3:45].C[SiH2]C>CN(C)C=O>[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH2:54][CH2:53][CH2:52][O:51][Si:48]([C:44]([CH3:45])([CH3:47])[CH3:46])([CH3:49])[CH3:50])[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 66185CID 66185HCID 3251421Potassium bis(trimethylsilyl)amideHCID 110051711-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl esterHCID 11022956Tert-butyl-(3-iodopropoxy)-dimethylsilane

Produkt 1

HCID 155242791-{[3-(Tert-butyl-dimethylsilanyloxy)-propyl]-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}cyclopentanecarboxylic acid benzyl esterAusbeute 103,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-[4-(4-fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester (199 grams, 0.42 mole) in dry N,N-dimethylformamide (2.5 L) at room temperature was added potassium hexamethyldisilazide (100 grams, 0.50 mole) and, after 3 hours, tert-butyl-(3-iodopropoxy)dimethylsilane (150 grams, 0.50 mole). The resulting mixture was stirred at room temperature for 16 hours. Additional tert-butyl-3-iodopropoxy)-dimethylsilane (20 grams, 0.067 mole) was then added. Stirring at room temperature was continued for a further 3.5 hours. The mixture was quenched by addition of saturated ammonium chloride solution. The N,N-dimethylformamide was removed by evaporation under vacuum. The residue was taken up in diethyl ether and washed with water and brine. After drying over magnesium sulfate, the diethyl ether was evaporated to afford crude 1-{[3-(tert-butyl-dimethylsilanyloxy)-propyl]-[4-(4-fluorophenoxy)benzenesulfonyl]-amino}cyclopentanecarboxylic acid benzyl ester as an amber oil (279.6 grams).

Aufarbeitung

  1. stirringStirring at room temperature
  2. waitwas continued for a further 3.5 hours
  3. customThe mixture was quenched by addition of saturated ammonium chloride solution
  4. customThe N,N-dimethylformamide was removed by evaporation under vacuum
  5. washwashed with water and brine
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe diethyl ether was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-91d9b349d20c410ea7159b4f5418a3a7
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06214872B1

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