2-Benzoylcyclohexanone → 2-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

HRID 479127

反応式

HRID 479127 の反応式
[CH2:1]([O:3][C:4](=[O:33])[CH:5]([NH2:32])[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[CH3:2].[C:34]([CH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][C:43]1=O)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1(OC)C=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4](=[O:33])[CH:5]([NH:32][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[C:34](=[O:41])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:9][CH:8]=1)[CH3:2]

参加物

5

反応物 2

HCID 2756272-BenzoylcyclohexanoneHCID 695578292-Amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester

生成物 1

HCID 695571212-(2-Benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester収率 15.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 7519Anisole溶媒

反応条件

温度
182.5 °C

実験手順

0.345 g of 2-Amino-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester was dissolved in 6 ml of anisole and treated successively with 0.181 g (1.15 eq.) of 2-benzoyl-cyclohexanone and 60 mg of Pd/C (10%) and heated under Ar to 180-185° C. After 80 Min., additional 60 mg of fresh catalyst was added and heating continued for another 3.5 h. Cooling to RT, pouring onto crashed ice, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and purification by flash chromatography (SiO2, hexane/AcOEt 7/3) produced 0.075 g of the title compound in the less polar fractions and 0.285 g of intermediate enamine, which was processed once again as just described. Final purification left a combined crop of 0.221 g of 2-(2-benzoyl-phenylamino)-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-naphthalen-1-yl}-propionic acid ethyl ester as yellow, sticky oil.

後処理

  1. temperatureheating
  2. temperatureCooling to RT
  3. additionpouring
  4. extractionice, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and purification by flash chromatography (SiO2, hexane/AcOEt 7/3)

出典と根拠

ORDレコード
ord-5090fdba31e7417fbcbb4338bb908c19
出典データセット
uspto-grants-2003_11
特許番号
US06642389B2

関連ノート

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