tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(2,2-difluorocyclopropyl)prop-2-enoate → HCID 117622748, compound

HRID 56811Notes

Reaction equation

HRID 56811 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:31]#[N:32])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([C:16](=[CH:24][CH:25]3[CH2:27][C:26]3([F:29])[F:28])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:30])[CH:9]=2)[CH:7]=1>[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:31]#[N:32])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:24][CH:25]3[CH2:27][C:26]3([F:29])[F:28])[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:10](=[O:30])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 118877865tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(2,2-difluorocyclopropyl)prop-2-enoate

Product 1

HCID 117622748HCID 117622748, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

At RT, 240 mg (purity 78%, 404 μmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(2,2-difluorocyclopropyl)prop-2-enoate (diastereomer mixture) were admixed with 30 ml of a “Hot Stryker's” reagent solution [B. A. Baker et al. Org. Lett. 2008, 10, 289-292]. The reaction mixture was stirred at RT for 2 h, and 20 ml of saturated aqueous ammonium chloride solution were then added. The phases were separated and the aqueous phase was extracted three times with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (40 g silica cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient). Yield: 216 mg (quant.)

Workup

  1. customAt RT
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted three times with 25 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography (40 g silica cartridge, 40 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-4882fb5d6bcf4bec8323c16481a11e8b
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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