Ammonium Chloride → tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoate

HRID 56886Notes

Reaction equation

HRID 56886 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][C:25]3([CH3:29])[CH2:28][O:27][CH2:26]3)[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][C:25]3([CH3:29])[CH2:26][O:27][CH2:28]3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:30])[CH:9]=2)[CH:7]=1

Participants

3

Reactant 2

HCID 25517Ammonium ChlorideHCID 118877923HCID 118877923, compound

Product 1

HCID 117622914tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-3-yl)propanoate

Procedure

At room temperature, 350 mg (766 μmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-methyloxetan-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 room temperature for 1 h, and saturated aqueous ammonium chloride solution was then added. After phase separation, the aqueous phase was extracted three times with 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, flow rate 40 ml/min, cyclohexane/ethyl acetate gradient). Yield: 345 mg (97% of theory)

Workup

  1. customAt room temperature
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted three times with 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, flow rate 40 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-61b37597ceb547199d98769897221455
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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