Sodium Chloride → 3-(2-Ethoxyethanoyl)-4-benzyloxazolidin-2-one

HRID 585008노트

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HRID 585008 반응식
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[CH2:25]([O:27][CH2:28][C:29](Cl)=[O:30])[CH3:26].[Cl-].[Na+]>C1COCC1>[CH2:25]([O:27][CH2:28][C:29]([N:9]1[CH:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])=[O:30])[CH3:26]

참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 84189Ethoxyacetyl chlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 178418244HCID 178418244, 화합물

생성물 1

HCID 219201173-(2-Ethoxyethanoyl)-4-benzyloxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

36.7 g (207 mmol) of (S)-4-benzyloxazolidin-2-one in 800 ml of THF are introduced into a round-bottomed flask under a stream of nitrogen. The reaction medium is cooled to −78° C. and 83 ml (207 mmol) of 2.5M n-butyllithium hexane are added dropwise. 30 minutes later, 25.4 g (207 mmol) of ethoxyacetyl chloride obtained in Example 81(b) are added, at −78° C. The reaction medium is stirred for 24 hours and then poured into saturated aqueous sodium chloride solution and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. After purification by chromatography on a column of silica eluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product are obtained in the form of an orange-colored oil.

후처리

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customAfter purification by chromatography on a column of silica
  6. washeluted with a heptane/ethyl acetate mixture (6/4), 30.6 g (56%) of the expected product
  7. customare obtained in the form of an orange-colored oil

출처 및 근거

ORD 기록
ord-87b9334d6a78453ab58a80b7a1cff62e
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06927228B2

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