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

HRID 2217745Notes

Reaction equation

HRID 2217745 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dc9248e4de204cb3a159ddb412bff18b
Source dataset
uspto-grants-2008_08
Patent number
US07408060B2

Reaction notes

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