Water → HCID 58452628, compound

HRID 70633Notes

Reaction equation

HRID 70633 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8](/[C:15](/[C:23]2[NH:28][C:27](=[O:29])[C:26]([CH:30]3[CH2:32][CH2:31]3)=[CH:25][CH:24]=2)=[CH:16]\[C@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[NH:18]2)[CH:9]=[CH:10][C:11]=1[O:12]CC.O>CCCCCC.C(Cl)(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8](/[C:15](/[C:23]2[NH:28][C:27](=[O:29])[C:26]([CH:30]3[CH2:32][CH2:31]3)=[CH:25][CH:24]=2)=[CH:16]\[C@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[NH:18]2)[CH:9]=[CH:10][C:11]=1[OH:12]

Participants

6

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 529509066-{(E)-1-(3-Chloro-4-ethoxyphenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one

Product 1

HCID 58452628HCID 58452628, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

A 1 M solution of boron tribromide in hexane (0.8 mL) was added to a solution of 6-{(E)-1-(3-chloro-4-ethoxyphenyl)-2-[(2R)-5-oxopyrrolidin-2-yl]ethenyl}-3-cyclopropylpyridin-2(1H)-one obtained in Example 4-10 (110 mg) in chloroform (2 mL), and the mixture was stirred at room temperature for two hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10) to give the title compound as a colorless amorphous (17.5 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0→90:10)

Sources & evidence

ORD record
ord-9e03c98d56ba46cd855fadc4bba1801a
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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