Hydrochloric Acid → HCID 15552091、化合物

HRID 587053ノート

反応式

HRID 587053 の反応式
[OH-].[Na+].[CH:3]([N:6]1C[CH2:9][CH2:8][C:7]1=O)([CH3:5])[CH3:4].Cl.[C:13](=[O:16])([O-])[O-:14].[Na+].[Na+].[Br:19][C:20]1[CH:21]=[CH:22][C:23](F)=[C:24]([CH:27]=1)[CH:25]=[O:26]>CS(C)=O>[Br:19][C:20]1[CH:21]=[CH:22][C:23]([N:6]([CH:3]([CH3:5])[CH3:4])[CH2:7][CH2:8][CH2:9][C:13]([OH:14])=[O:16])=[C:24]([CH:25]=[O:26])[CH:27]=1

参加物

7

反応物 5

HCID 313Hydrochloric Acid2 回HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 77392N-IsopropylbutyrolactamHCID 7363275-Bromo-2-fluorobenzaldehyde

生成物 1

HCID 15552091HCID 15552091、化合物収率 7.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

4N sodium hydroxide (36 ml) was added to 1-isopropyl-2-pyrrolidone (9.2 g), and the mixture was stirred for 3.5 hours. After cooled to 0° C., the mixture was neutralized with concentrated hydrochloric acid. After sodium carbonate (15.3 g) was added thereto, a solution of 5-bromo-2-fluorobenzaldehyde (7.3 g) in dimethyl sulfoxide (96 ml) was added thereto, and the mixture was heated to reflux for 5 hours. After cooled to room temperature, pH was adjusted to approximate 4 with 6N hydrochloric acid, and the mixture was extracted with ethyl acetate/THF. The extract was washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2) to give 4-(4-bromo-2-formylisopropylanilino)butyric acid (0.92 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 5 hours
  3. temperatureAfter cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate/THF
  5. washThe extract was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=4/1→3/2)

出典と根拠

ORDレコード
ord-e17d7eef7a4547969de5e0a5055c0b58
出典データセット
uspto-grants-2005_08
特許番号
US06936602B1

反応ノート

読み込み中…