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Ammonium Chloride → Rac-5-{2-ethinyl-2-hydroxy-3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-propionylamino}phthalide

HRID 2217745
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HRID 2217745 반응식
[C:1]([Mg]Br)#[CH:2].[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:34])[C:21]([NH:23][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[C:29](=[O:30])[O:28][CH2:27]3)=[O:22])[CH2:18][CH2:17]1.[Cl-].[NH4+]>C1COCC1>[C:1]([C:20]([OH:34])([CH2:19][C:16]1([C:7]2[CH:8]=[C:9]([C:12]([F:15])([F:13])[F:14])[CH:10]=[CH:11][C:6]=2[F:5])[CH2:18][CH2:17]1)[C:21]([NH:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:29](=[O:30])[O:28][CH2:27]2)=[O:22])#[CH:2]
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참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 688712075-{3-[1-(2-Fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxo-propionylamino}-phthalideHCID 178418486HCID 178418486, 화합물

생성물 1

HCID 58900308Rac-5-{2-ethinyl-2-hydroxy-3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-propionylamino}phthalide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Ethinyl magnesium bromide (6 ml, 0.5 M in tetrahydrofuran) was added to an ice-cold solution that consists of 5-{3-[1-(2-fluoro-5-trifluoromethylphenyl)-cyclopropyl]-2-oxopropionylamino}phthalide (632 mg) in THF (4 ml). The reaction solution under argon was allowed to come to room temperature within 3 hours. Then, the reaction mixture was poured into ice-cold, saturated ammonium chloride solution. It was extracted with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution and dried on sodium sulfate. The crude product that is obtained was chromatographed on silica gel. 2.2 g of product was obtained.

후처리

  1. extractionIt was extracted with ethyl acetate
  2. washThe combined organic phases were washed with saturated sodium chloride solution
  3. customdried on sodium sulfate
  4. customThe crude product that is obtained
  5. customwas chromatographed on silica gel

출처 및 근거

ORD 기록
ord-dc9248e4de204cb3a159ddb412bff18b
출처 데이터셋
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07408060B2

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