Potassium Carbonate → Ethyl 3-({[3-(4-chlorophenyl)-isoxazol-5-yl]methyl}amino)-3-methylbutanoate

HRID 1485120ノート

反応式

HRID 1485120 の反応式
Cl.[NH2:2][C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:13][C:14]1[O:18][N:17]=[C:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:15]=[C:14]([CH2:13][NH:2][C:3]([CH3:11])([CH3:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[O:18][N:17]=2)=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 21369Isoxazole, 5-bromomethyl-3-(p-chlorophenyl)-HCID 15578558Ethyl 3-amino-3-methylbutanoate hydrochloride

生成物 1

HCID 118113168Ethyl 3-({[3-(4-chlorophenyl)-isoxazol-5-yl]methyl}amino)-3-methylbutanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
60 °C

実験手順

To a solution of ethyl 3-amino-3-methylbutyrate hydrochloride (333 mg) in tetrahydrofuran (4.00 mL), a solution in tetrahydrofuran (2.00 mL) of the compound (100 mg) obtained in step (2) above and potassium carbonate (406 mg) were added and the mixture was stirred at 60° C. for three days. After passing the reaction mixture through Celite (registered trademark), the filtrate was concentrated under reduced pressure and the resulting residue was roughly purified by preparative HPLC. To the resulting roughly purified product, a saturated aqueous solution of sodium hydrogencarbonate was added and extraction was conducted with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and after removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-50:50) to give the titled compound as a colorless amorphous mass.

後処理

  1. concentrationthe filtrate was concentrated under reduced pressure
  2. customthe resulting residue was roughly purified by preparative HPLC
  3. additionTo the resulting roughly purified product, a saturated aqueous solution of sodium hydrogencarbonate was added
  4. extractionextraction
  5. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  6. customafter removing the
  7. filtrationdesiccant by filtration
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-50:50)

出典と根拠

ORDレコード
ord-bc78b860e859498dabe736749cb07bff
出典データセット
uspto-grants-2016_08
特許番号
US09422240B2

反応ノート

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