tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate → HCID 117622711, compound

HRID 56874Notes

Reaction equation

HRID 56874 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]#[N:33])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([C:16](=[CH:24][C:25]3([CH2:29][CH3:30])[CH2:28][O:27][CH2:26]3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:31])[CH:9]=2)[CH:7]=1>[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]#[N:33])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:24][C:25]3([CH2:29][CH3:30])[CH2:26][O:27][CH2:28]3)[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:10](=[O:31])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 1

HCID 118877902tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate

Product 1

HCID 117622711HCID 117622711, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

At RT, 302 mg (641 μmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate (isomer mixture) were admixed with 20 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 1.5 h, and 20 ml of saturated aqueous ammonium chloride solution were then added. After phase separation, 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 (120 g silica cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient). Yield: 275 mg (91% of theory)

Workup

  1. customAt RT
  2. customAfter phase separation
  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 (120 g silica cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-de808c8ef73647fda2f4c448aee70f9d
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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