4-Cyclohexylphenol → (S)-2-(4-cyclohexyl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

HRID 237753

反応式

HRID 237753 の反応式
[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.[CH:26]1([C:32]2C=C[C:35]([OH:38])=[CH:34][CH:33]=2)CCCCC1.C(OCC)(=O)C#CCC>C(O)C>[CH:1]1([C:7]2[CH:20]=[CH:19][C:10]([O:11][CH2:12][C@H:13]3[O:17][C:16]4=[N:18][C:35](=[O:38])[CH:34]=[C:33]([CH2:32][CH3:26])[N:15]4[CH2:14]3)=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

6

反応物 4

HCID 143274-CyclohexylphenolHCID 99169Ethyl pent-2-yn-1-oateHCID 2734062(-)-EpichlorohydrinHCID 66875140(S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine

生成物 1

HCID 25074223(S)-2-(4-cyclohexyl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of (S)-5-(4-cyclohexyl-phenoxymethyl)-4,5-dihydro-oxazol-2-ylamine (1.0 g, 3.64 mmol), prepared in accordance with the procedures as set forth in Steps 1 and 2 of Example 1 and starting from R-epichlorohydrin and 4-cyclohexylphenol, in ethanol (18.2 mL) was added ethyl 2-pentynoate (0.92 g, 7.28 mmol). The reaction mixture was heated at reflux for 14 hrs and then gradually cooled to room temperature. The resulting crystalline solid was isolated by filtration, washed with heptane 3 times, and dried under vacuum to afford 560 mg of (S)-2-(4-cyclohexyl-phenoxymethyl)-5-ethyl-2,3-dihydro-oxazolo[3,2-a]pyrimidin-7-one as a white solid. [α]D25 −27.96 (c 0.526, CHCl3).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 14 hrs
  3. customThe resulting crystalline solid was isolated by filtration
  4. washwashed with heptane 3 times
  5. customdried under vacuum

出典と根拠

ORDレコード
ord-1892876516164c2fa586556fdba07101
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

関連ノート

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