Dicyclohexylcarbodiimide → (RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrate

HRID 34599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 34599
C1(N=C=NC2CCCCC2)CCCCC1.[CH3:16][C:17]([C:20]1[N:25]=[CH:24][C:23]([CH:26]([CH:30]([CH3:32])[CH3:31])[C:27]([OH:29])=[O:28])=[CH:22][N:21]=1)([CH3:19])[CH3:18].[C:33]([CH:35](O)[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:37]=1)#[CH:34]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:19][C:17]([C:20]1[N:21]=[CH:22][C:23]([CH:26]([CH:30]([CH3:32])[CH3:31])[C:27]([O:29][CH:35]([C:33]#[CH:34])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([O:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:37]=2)=[O:28])=[CH:24][N:25]=1)([CH3:16])[CH3:18]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 129190923-Phenoxy-alpha-ethynylbenzylalcoholHCID 13911492(RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyric acid

Produkt 1

HCID 13911493(RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrateAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N,N'-dicyclohexylcarbodiimide (0.2 g) in dichloromethane (5 cm3) was added to a stirred mixture of (RS)-2-[2-(2-methylprop-2-yl)pyrimidin-5-yl]-3-methylbutyric acid (0.26 g), (RS)-α-ethynyl-3-phenoxybenzyl alcohol (0.224 g), 4-dimethylaminopyridine (0.02 g) and dry dichloromethane (5 cm3) and the resultant mixture stirred for 2 hours. The precipitate which formed was removed by filtration and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residual oil was purified by column chromatography using a silica column eluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60° to 80° C., 1 part by volume) to yield (RS)-1-ethynyl-1-(3-phenoxyphenyl)methyl (RS)-2-[2-(2-methylprop-2-yl)-pyrimidin-5-yl]-3-methylbutyrate (0.4g), as a mixture of diastereoisomers.

Aufarbeitung

  1. customThe precipitate which formed
  2. customwas removed by filtration
  3. concentrationthe filtrate concentrated by evaporation of the solvent under reduced pressure
  4. customThe residual oil was purified by column chromatography
  5. washeluted with a mixture of ethyl acetate (1 part by volume) and petroleum ether (boiling range 60° to 80° C., 1 part by volume)

Quellen und Nachweise

ORD-Eintrag
ord-c386507b28164d92ae62632ecf157c70
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04762835

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