Hydrochloric Acid → 5-{3-[1-(2-Fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalide

HRID 132511

反応式

HRID 132511 の反応式
S(Cl)(Cl)=O.[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[C:16]1([CH2:19][C:20](=[O:24])[C:21](O)=[O:22])[CH2:18][CH2:17]1.[NH2:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[C:31](=[O:32])[O:30][CH2:29]2.Cl>CC(N(C)C)=O.C(OCC)(=O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][C:7]=1[C:16]1([CH2:19][C:20](=[O:24])[C:21]([NH:25][C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[C:31](=[O:32])[O:30][CH2:29]3)=[O:22])[CH2:17][CH2:18]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 7206695-Aminophthalide2 回HCID 688415163-[1-(2-Fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionic acid

生成物 1

HCID 688712075-{3-[1-(2-Fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalide

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
0 °C

実験手順

At −10° C., 0.84 ml of thionyl chloride are added to 2.9 g of 3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionic acid in 15 ml dimethylacetamide. The mixture is stirred for 30 min. at −10° C. and for 1 hour at 0° C. and then added to 1.95 g of 5-aminophthalide (or, vice versa, 5-aminophthalide may be added to the mixture). After 16 hours at ambient temperature, 2 M hydrochloric acid and ethyl acetate are added, the organic phase is washed to neutral with water, dried over sodium sulfate and concentrated. After chromatography on silica gel (hexane/ethyl acetate: 1+1) and recrystallization from diisopropyl ether, 2.4 g of 5-{3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalide (m.p. 168° C.) are obtained.

後処理

  1. additionmay be added to the mixture)
  2. waitAfter 16 hours at ambient temperature
  3. washthe organic phase is washed to neutral with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customAfter chromatography on silica gel (hexane/ethyl acetate: 1+1) and recrystallization from diisopropyl ether, 2.4 g of 5-{3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalide (m.p. 168° C.)
  7. customare obtained

出典と根拠

ORDレコード
ord-0d1bfca890c446e988feafadab5cd626
出典データセット
uspto-grants-2008_06
特許番号
US07388006B2

関連ノート

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