Ammonium Chloride → (-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamide

HRID 541138ノート

反応式

HRID 541138 の反応式
C(N1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21](O)=O)[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:27])([F:26])[F:25])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)C.Cl.CN(C)[CH2:32][CH2:33]CN=C=NCC.[OH2:41].O[N:43]1C2C=CC=CC=2N=N1.[Cl-].[NH4+:53]>C(OCC)(=O)C.C(N(CC)CC)C.CN(C)C=O>[CH2:32]([N:53]1[CH:7]=[C:6]([C:8]2[CH:20]=[C:19]([C:21]([NH2:43])=[O:41])[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:11]([OH:28])([C:24]([F:25])([F:27])[F:26])[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)[CH3:33]

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 594931002-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid

生成物 1

HCID 46191680(-)-2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxamide収率 85%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a mixture of an optically active form (0.051 g) of 2-(1-ethyl-1H-pyrazol-4-yl)-9-hydroxy-9-trifluoromethyl-9H-fluorene-4-carboxylic acid, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.038 g), 1-hydroxybenzotriazole hydrate (0.030 g), ammonium chloride (0.022 g) and dimethylformamide (1 ml) was added triethylamine (0.055 ml), and the mixture was stirred at room temperature overnight. To the reaction mixture was added ethyl acetate (10 ml), and the organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (0.043 g, 85%).

後処理

  1. washthe organic layer was successively washed once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate, 3 times with water and once with saturated brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-2c907d052c3749479956d85bb85ad877
出典データセット
uspto-grants-2014_10
特許番号
US08871934B2

反応ノート

読み込み中…