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Ethyl Acetate → (R)-3-{4-[4-(3,5-dichloropyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methoxymethyloxazolidin-2-one

HRID 1804243
Notes
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Reaction equation

HRID 1804243 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[N:16]1[C@H:20]([CH2:21][O:22][CH3:23])[CH2:19][O:18][C:17]1=[O:24].Cl[C:26]1[C:31]([Cl:32])=[CH:30][C:29]([Cl:33])=[CH:28][N:27]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:32][C:31]1[C:26]([N:13]2[CH2:14][CH2:15][N:10]([C:8]([C:6]3[CH:5]=[CH:4][C:3]([N:16]4[C@H:20]([CH2:21][O:22][CH3:23])[CH2:19][O:18][C:17]4=[O:24])=[C:2]([F:1])[CH:7]=3)=[O:9])[CH2:11][CH2:12]2)=[N:27][CH:28]=[C:29]([Cl:33])[CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 276662,3,5-TrichloropyridineHCID 58484520(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one

Product 1

HCID 67381023(R)-3-{4-[4-(3,5-dichloropyridin-2-yl)piperazine-1-carbonyl]-2-fluorophenyl}-4-methoxymethyloxazolidin-2-oneYield 48.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one (343 mg) described in Preparation Example 94 was dissolve in N,N-dimethylformamide (2 mL), 2,3,5-trichloropyridine (275 mg) and potassium carbonate (562 mg) were added and the mixture was stirred at 100° C. To the reaction mixture was added ethyl acetate under ice-cooling and insoluble materials were filtered off. Water was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (chloroform:methanol) to give the title compound (240 mg).

Workup

  1. temperaturecooling
  2. filtrationinsoluble materials were filtered off
  3. additionWater was added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed twice with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-d0ef9fe2334f420e8ca0f70bd1621424
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354401B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes