Heptanoyl chloride → 3-Heptanoyl-4-(S)-isopropyl-oxazolidin-2-one

HRID 263438

反応式

HRID 263438 の反応式
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[NH:5]1)([CH3:3])[CH3:2].C([Li])CCC.[C:15](Cl)(=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Cl-].[NH4+]>O1CCCC1>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:15](=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 17313Heptanoyl chlorideHCID 25517Ammonium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

生成物 1

HCID 108576323-Heptanoyl-4-(S)-isopropyl-oxazolidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-(S)-isopropyl-2-oxazolidinone (5.04 g) in tetrahydrofuran (125 ml) was cooled to -78° C. under an atmosphere Of nitrogen. n-Butyl lithium (16 ml, 1.65M, in hexane).was added dropwise to the solution. Heptanoyl chloride (6.4 ml) was added to the resulting mixture after 10 min stirring, and the stirring was continued for another 1.5 hours at the same temperature. The reaction mixture was then poured into a 5% aqueous solution of ammonium chloride and was extracted with ethyl acetate. The organic extract was successively washed with water and a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by column chromatography through silica gel, using a 8:1 mixture of hexane and ethyl acetate as an eluent, to give the desired compound (9.69 g) as a colorless oil.

後処理

  1. extractionwas extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas successively washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over sodium sulfate
  5. distillationAfter the solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography through silica gel
  7. additiona 8:1 mixture of hexane and ethyl acetate as an eluent

出典と根拠

ORDレコード
ord-01e3fa91f7ca4602a9d786535b58ac00
出典データセット
uspto-grants-1997_07
特許番号
US05643908

関連ノート

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