1-Hydroxybenzotriazole hydrate → (4-(5-(3-Chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

HRID 1777360

反応式

HRID 1777360 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=O.O[NH:16][C:17](=[NH:26])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=1.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:26]=[C:17]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=3)[N:16]=2)[CH:8]=[CH:9][C:10]=1[CH2:11][CH:12]([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 27960291-Hydroxybenzotriazole hydrateHCID 593167203-chloro-4-(2-methylpropyl)Benzoic acidHCID 178513316HCID 178513316、化合物

生成物 1

HCID 70869326(4-(5-(3-Chloro-4-isobutylphenyl)-1,2,4-oxadiazol-3-yl)phenyl)methanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
122.5 °C

実験手順

N,N-Dicyclohexylcarbodiimide (1.07 g, 0.0052 mol) is added to a solution of 3-chloro-4-isobutylbenzoic acid (0.74 g, 0.0035 mol), N-hydroxy-4-hydroxymethylbenzamidine (0.867 g, 0.0052 mol) and N-hydroxybenzotriazole monohydrate (0.798 g, 0.0052 mol) in N,N-dimethylformamide (15 mL). The reaction mixture is heated at 120-125° C. for 2 hrs. It is then cooled to 0-5° C., filtered and washed with dichloromethane (2×20 mL). The filtrate is evaporated under reduced pressure and the residue is treated with demineralized water (20 mL). It is extracted with ethyl acetate (2×30 mL) and the combined extract is dried over sodium sulfate. Removal of solvent under reduced pressure gives a crude residue which is purified by column chromatography (silica gel 230-400, ethyl acetate:toluene, 15:85) to give {4-[5-(3-chloro-4-isobutylphenyl)-[1,2,4]-oxadiazol-3-yl]-phenyl}methanol.

後処理

  1. temperatureIt is then cooled to 0-5° C.
  2. filtrationfiltered
  3. washwashed with dichloromethane (2×20 mL)
  4. customThe filtrate is evaporated under reduced pressure
  5. additionthe residue is treated with demineralized water (20 mL)
  6. extractionIt is extracted with ethyl acetate (2×30 mL)
  7. extractionthe combined extract
  8. dry with materialis dried over sodium sulfate
  9. customRemoval of solvent under reduced pressure
  10. customgives a crude residue which
  11. customis purified by column chromatography (silica gel 230-400, ethyl acetate:toluene, 15:85)

出典と根拠

ORDレコード
ord-009c44ae601f4be8b37956c68656d75a
出典データセット
uspto-grants-2016_02
特許番号
US09266867B2

関連ノート

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