Lithium Hydroxide → 4-(5-Undecyl-pyrimidin-2-yl)phenyl 3-propyloxy-isoxazole-5-carboxylate

HRID 1826551

Reaktionsgleichung

Reaktionsgleichung von HRID 1826551
[CH2:1]([C:12]1[CH:13]=[N:14][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[N:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[CH2:25]([O:28][C:29]1[CH:33]=[C:32]([C:34](O)=[O:35])[O:31][N:30]=1)[CH2:26][CH3:27].OC1C=C(C(OC)=O)ON=1.BrCCC.[Li+].[OH-].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].O1CCCC1.ClCCl>[CH2:25]([O:28][C:29]1[CH:33]=[C:32]([C:34]([O:24][C:21]2[CH:20]=[CH:19][C:18]([C:15]3[N:16]=[CH:17][C:12]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])=[CH:13][N:14]=3)=[CH:23][CH:22]=2)=[O:35])[O:31][N:30]=1)[CH2:26][CH3:27]

Komponenten

10

Edukt 6

HCID 3939Lithium HydroxideHCID 78401-BromopropaneHCID 10868DicyclohexylcarbodiimideHCID 221342243-Propoxyisoxazole-5-carboxylic acidHCID 1356196824-(5-Undecylpyrimidin-2-yl)phenolHCID 178498603HCID 178498603, Verbindung

Produkt 1

HCID 221342394-(5-Undecyl-pyrimidin-2-yl)phenyl 3-propyloxy-isoxazole-5-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 86662288HCID 86662288, VerbindungLösungsmittel

Versuchsvorschrift

4.9 g of 4-(5-undecyl-pyrimidin-2-yl)phenol, 1.7 g of 3-propyloxy-isoxazole-5-carboxylic acid (prepared as described by Xue et al., Bioorg. Med. Chem. Letters 8 (1998) 3499 by reacting methyl 3-hydroxy-isoxazole-5-carboxylate, which is commercially available, with 1-bromopropane at 60° C. in dimethylformamide/potassium carbonate followed by hydrolysis with LiOH in tetrahydrofuran) and 2.1 g of dicyclohexylcarbodiimide are stirred for 24 h in 50 ml of dichloromethane at room temperature. Filtration, removal of the dichloromethane by distillation, purification by chromatography (silica gel; dichloromethane/heptane) and recrystallization from acetonitrile affords the target compound as colorless crystals having the phase sequence X 91 SA 109 N 126 I.

Aufarbeitung

  1. filtrationFiltration, removal of the dichloromethane
  2. distillationby distillation, purification
  3. customby chromatography (silica gel; dichloromethane/heptane) and recrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-a327110eb985418eb6bfdfa87d7228e8
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07052742B1

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