Hydrochloric Acid → (R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl ester

HRID 1804039Notes

Reaction equation

HRID 1804039 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:38])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][O:27]C(=O)C4C=CC=CC=4)[CH2:24][O:23][C:22]3=[O:36])=[C:17]([F:37])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.[Cl-].[Na+]>C(COC)OC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14](=[O:38])[C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C@H:25]([CH2:26][OH:27])[CH2:24][O:23][C:22]3=[O:36])=[C:17]([F:37])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 54755120(R)-4-[4-(4-benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 58484618(R)-4-[3-fluoro-4-(4-hydroxymethyl-2-oxooxazolidin-3-yl)benzoyl]piperazine-1-carboxylic acid tert-butyl esterYield 73.8%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(R)-4-[4-(4-Benzoyloxymethyl-2-oxooxazolidin-3-yl)-3-fluoro-benzoyl]piperazine-1-carboxylic acid tert-butyl ester (1.45 g) described in Preparation Example 91 was dissolved in dimethoxyethane, 4N aqueous sodium hydroxide solution was added and the mixture was stirred at room temperature. Under ice-cooling, the reaction mixture was neutralized with 1N hydrochloric acid, ethyl acetate and sodium chloride were added and the mixture was extracted with ethyl acetate, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (859 mg).

Workup

  1. temperatureUnder ice-cooling
  2. additionwere added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-2aa30956c3dd4c6393c4192bef09a111
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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