Dimethylformamide → 3-Benzyloxy-6-methyl-4-oxo-4H-pyran-2-carboxylic acid cyclohexylamide

HRID 2218107ノート

反応式

HRID 2218107 の反応式
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].C[C:14]1[O:19][C:18]([C:20](O)=O)=[CH:17][C:16](=[O:23])[CH:15]=1.[CH:24]1(N)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.CN(C)[CH:33]=[O:34]>>[CH:12]1([NH:8][C:1]([C:14]2[O:19][C:18]([CH3:20])=[CH:17][C:16](=[O:23])[C:15]=2[O:34][CH2:33][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:2])[CH2:11][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 7965CyclohexylamineHCID 682631,1'-CarbonyldiimidazoleHCID 4229426-Methyl-4-oxo-4H-pyran-2-carboxylic acid

生成物 1

HCID 866117973-Benzyloxy-6-methyl-4-oxo-4H-pyran-2-carboxylic acid cyclohexylamide収率 61%

実験手順

1,1′-carbonyldiimidazole (1.99 g, 12.30 mmol) was added to a solution of the 3-(benzyloxy,-6-methyl-4-oxo-4H-pyran-2-carboxylic acid (2.0 g, 7.69 mmol) in dimethylformamide (DMF, 18 ml) at room temperature. The resulting solution was heated at 40°-50° C. for 3 hrs. A light yellow solution was observed. Cyclohexylamine (1.23 ml, 10.76 mmol) was then added. The resulting mixture was stirred at room temperature for overnight. The DMF was removed under reduced pressure to give light yellow oil as a crude product, which was purified by flash column chromatography (elution gradient: from 1:1 ethyl acetate/hexane to 10% methanol in ethyl acetate) to yield the titled compound (1.60 g, yield 61%) as white solid.

後処理

  1. customat room temperature
  2. temperatureThe resulting solution was heated at 40°-50° C. for 3 hrs
  3. customThe DMF was removed under reduced pressure
  4. customto give light yellow oil as a crude product, which
  5. customwas purified by flash column chromatography (elution gradient: from 1:1 ethyl acetate/hexane to 10% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-6feb1049c93c433aa74c70ecf8a045e3
出典データセット
uspto-grants-2008_08
特許番号
US07410985B2

反応ノート

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