4-Cyclohexylphenol → (S)-2-(4-cyclohexyl-phenoxymethyl)-7-oxo-2,3-dihydro-7H-oxazolo[3,2-a]pyrimidine-5-carboxylic acid ethyl ester

HRID 237814

Reaktionsgleichung

Reaktionsgleichung von HRID 237814
[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]([NH2:18])=[N:15][CH2:14]3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1O[C@H]1CCl.C1(C2C=CC(O)=CC=2)CCCCC1.[C:39]([C:46](OCC)=[O:47])#[C:40][C:41]([O:43][CH2:44][CH3:45])=[O:42]>C(O)C>[CH2:44]([O:43][C:41]([C:40]1[N:15]2[CH2:14][C@@H:13]([CH2:12][O:11][C:10]3[CH:19]=[CH:20][C:7]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:8][CH:9]=3)[O:17][C:16]2=[N:18][C:46](=[O:47])[CH:39]=1)=[O:42])[CH3:45]

Komponenten

6

Edukt 4

HCID 143274-CyclohexylphenolHCID 69803Diethyl acetylenedicarboxylateHCID 2734062(-)-EpichlorohydrinHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

Produkt 1

HCID 25069510(S)-2-(4-cyclohexyl-phenoxymethyl)-7-oxo-2,3-dihydro-7H-oxazolo[3,2-a]pyrimidine-5-carboxylic acid ethyl esterAusbeute 58,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (0.5 g, 1.82 mmol), prepared in accordance with the procedures described in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol, in ethanol (10 mL) was added diethyl acetylenedicarboxylate (0.39 g, 2.29 mmol). The reaction mixture was heated at reflux for 14 hours and then stored in a freezer overnight. The reaction mixture was warmed to room temperature. The resulting crystalline solid was isolated by centrifugation and dried under vacuum at 60° C. to afford 427 mg of (S)-2-(4-cyclohexyl-phenoxymethyl)-7-oxo-2,3-dihydro-7H-oxazolo[3,2-a]pyrimidine-5-carboxylic acid ethyl ester. [α]D25 −16.15 (c 0.52, CHCl3).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 14 hours
  3. customThe resulting crystalline solid was isolated by centrifugation
  4. customdried under vacuum at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-f04a2079081a4dda8d70ba64ad20b47c
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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