1,2-Dichloroethane → 1-(cyclohexylacetyl)-4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine

HRID 1850770Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850770
[N:1]1([C:6]2[CH:23]=[CH:22][C:9]([O:10][CH2:11][CH2:12][C@@H:13]3[CH2:15][C@@H:14]3[CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[CH:24]1([CH2:30][C:31](O)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[CH:24]1([CH2:30][C:31]([N:19]2[CH2:20][CH2:21][CH:16]([C@H:14]3[CH2:15][C@H:13]3[CH2:12][CH2:11][O:10][C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH:5]=[N:4][N:3]=[N:2]4)=[CH:23][CH:22]=3)[CH2:17][CH2:18]2)=[O:32])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 21363Cyclohexaneacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 867111854-((1R,2S)-2-(2-(4-(1H-tetrazol-1-yl)phenoxy)ethyl)cyclopropyl)piperidine

Produkt 1

HCID 708560481-(cyclohexylacetyl)-4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 23 mg (0.071 mmol) of 4-((1R,2S)-2-{2-[4-(1H-tetrazol-1-yl)phenoxy]ethyl}cyclopropyl)piperidine in 0.6 ml anhydrous N,N-dimethylformamide at ambient temperature was added 0.020 ml (0.14 mmol) cyclohexylacetic acid, followed by 27 mg (0.14 mmol) EDC, 9.6 mg (0.071 mmol) HOBt, and 0.062 ml (0.35 mmol) diisopropylethylamine. The solution was stirred overnight at ambient temperature. The crude in N,N-dimethylformamide was purified directly by reverse phase HPLC (TMC Pro-Pac C18; 30-100% acetonitrile/0.1% formic acid in water gradient). The pure fractions were lyophilized to yield the title compound as white solid.

Aufarbeitung

  1. customThe crude in N,N-dimethylformamide was purified directly by reverse phase HPLC (TMC Pro-Pac C18; 30-100% acetonitrile/0.1% formic acid in water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-b3b30a0e27df4280a14fbc71fa44e6e3
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957062B2

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