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Hydrochloric Acid → (2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanol

HRID 356822
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HRID 356822 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:23])([CH2:17][O:18]S(C)(=O)=O)[CH2:10]OC(=O)C(C)C.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:23][CH2:10]1)[CH2:17][OH:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11279597(S)-2-(2,4-difluorophenyl)-1-isobutyryloxy-3-methanesulfonyloxy-2-propanol

생성물 1

HCID 10176425(2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanol수율 95.1%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

In 14 ml of methanol was dissolved 4.06 g of (S)-2-(2,4-difluorophenyl)-1-isobutyryloxy-3-methanesulfonyloxy-2-propanol obtained in Example 44. After a temperature of the resulting liquid was kept at 5° C., 14 ml of aqueous solution of 2N sodium hydroxide was added dropwise thereto with cooling at 15° C. or below. After dropping, the resulting liquid was stirred at a temperature of 10° to 15° C. for 2 hours. Thereto 1N hydrochloric acid was added until the liquid was adjusted to pH 7 and methanol was removed under reduced pressure. To the residue was added ethyl acetate to extract. The resulting organic layer was washed with saturated aqueous solution with sodium chloride. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1) to give 2.04 g of oily (S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-propanol. An optical purity thereof was determined in the same manner as in Example 35. (Elution time: 9.24 minutes ((S)-form) and 10.7 minutes ((R)-form)).

후처리

  1. customwas kept at 5° C.
  2. temperaturewith cooling at 15° C. or below
  3. customwas removed under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. extractionto extract
  6. washThe resulting organic layer was washed with saturated aqueous solution with sodium chloride
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-3a1260f19cc74e63b479be9c42fc6fa6
출처 데이터셋
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05840553

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