Sodium Bicarbonate → (R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-one

HRID 1804041Notes

Reaction equation

HRID 1804041 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:31])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][O:27][CH3:28])[CH2:24][O:23][C:22]3=[O:29])=[C:17]([F:30])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[F:30][C:17]1[CH:16]=[C:15]([C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:31])[CH:20]=[CH:19][C:18]=1[N:21]1[C@H:25]([CH2:26][O:27][CH3:28])[CH2:24][O:23][C:22]1=[O:29]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 54755121(R)-4-[3-fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58484520(R)-3-[2-fluoro-4-(piperazine-1-carbonyl)phenyl]-4-methoxymethyloxazolidin-2-oneYield 99.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-4-[3-Fluoro-4-(4-methoxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester (506 mg) described in Preparation Example 93 was dissolved in ethyl acetate (5 mL), 4N hydrogen chloride/ethyl acetate (5 mL) was added and the mixture was stirred at room temperature. Under ice-cooling, the reaction mixture was neutralized with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution, and extracted once with ethyl acetate and the aqueous layer was extracted with twice with chloroform. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (390 mg).

Workup

  1. temperatureUnder ice-cooling
  2. extractionextracted once with ethyl acetate
  3. extractionthe aqueous layer was extracted with twice with chloroform
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-51b2e81de1a74df5b02afdb6d60c1568
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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