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

HRID 420473노트

반응식

HRID 420473 반응식
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:20][C:21]1[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])[O:23][C:22]=1[C:29]([OH:31])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH:32]1([NH2:38])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>CN(C)C=O>[CH:32]1([NH:38][C:29]([C:22]2[O:23][C:24]([CH3:28])=[CH:25][C:26](=[O:27])[C:21]=2[O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:31])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

참가 물질

5

반응물 3

HCID 7965CyclohexylamineHCID 682631,1'-CarbonyldiimidazoleHCID 98564973-(benzyloxy)-6-methyl-4-oxo-4H-pyran-2-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-1b89491ab49f4956a726c90df2609b3f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097624B2

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