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

HRID 1804039ノート

反応式

HRID 1804039 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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).

後処理

  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)

出典と根拠

ORDレコード
ord-2aa30956c3dd4c6393c4192bef09a111
出典データセット
uspto-grants-2013_01
特許番号
US08354401B2

反応ノート

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