Benzoic Acid → 1-Benzoyl-4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

HRID 1873833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1873833
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:6])=[O:5])[CH3:3].[C:23](O)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:23]([N:20]1[CH2:21][CH2:22][CH:17]([C:2]([CH3:1])([S:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=2)(=[O:5])=[O:6])[CH3:3])[CH2:18][CH2:19]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Komponenten

6

Edukt 4

HCID 243Benzoic AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Produkt 1

HCID 252556891-Benzoyl-4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a 10 ml vial was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (33 mg, 0.098 mmol), benzoic acid (10 mg, 0.082 mmol), Bop reagent (43.5 mg, 0.098 mmol), diisopropylethyl amine (0.029 ml, 0.164 mmol) and 2 ml dimethylformamide. The resulting solution was stirred at room temperature for 10 minutes. LC-Mass showed clean desired product. The reaction mixture was diluted with 1 ml dimethyl sulfoxide, 1 ml water and 0.03 ml of trifluoroacetic acid. This mixture was loaded on a reverse phase column and purified on HPLC eluted with water/acetonitrile gradient solvent. Desired fraction was collected and lyophilized to give the title compound as a fluffy white solid.

Quellen und Nachweise

ORD-Eintrag
ord-e4eec2dab9a241a8a6f525743aca72e0
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304434B2

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