Acetic Anhydride → Ralaniten Acetate

HRID 705324노트

반응식

HRID 705324 반응식
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][CH2:9][C@@H:10]([OH:34])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:22]2[CH:33]=[CH:32][C:25]([O:26][CH2:27][C@H:28]([OH:31])[CH2:29][OH:30])=[CH:24][CH:23]=2)([CH3:21])[CH3:20])=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:11]([O:30][CH2:29][C@@H:28]([O:31][C:5](=[O:7])[CH3:6])[CH2:27][O:26][C:25]1[CH:24]=[CH:23][C:22]([C:19]([C:16]2[CH:15]=[CH:14][C:13]([O:12][CH2:11][C@H:10]([O:34][C:25](=[O:26])[CH3:24])[CH2:9][Cl:8])=[CH:18][CH:17]=2)([CH3:21])[CH3:20])=[CH:33][CH:32]=1)(=[O:12])[CH3:10]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 45107537Ralaniten

생성물 1

HCID 86278934Ralaniten Acetate수율 182.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

Acetic Anhydride (4.3 g, 41.7 mmol) was added to a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (2.8 g, 6.95 mmol) and DMAP (30 mg, 0.25 mmol) in anhydrous pyridine (24 mL) in a water bath. The resulting solution was stirred overnight. The pyridine was removed under reduced pressure and the residue was diluted with ethyl acetate (50 mL), washed subsequently with water (2×40 mL), then cold aqueous 1M HCl (40 mL), saturated NaHCO3 (40 mL) and water (40 mL). The organic layer was dried over Mg2SO4, filtered and concentrated to give light yellow oil. The crude product was purified by column chromatography (eluent: 5% ethyl acetate in hexane to 20% ethyl acetate in hexane) to afford the title compound (3.30 g, 91.5% yield) as a colorless viscous oil.

후처리

  1. customThe pyridine was removed under reduced pressure
  2. additionthe residue was diluted with ethyl acetate (50 mL)
  3. washwashed subsequently with water (2×40 mL)
  4. dry with materialThe organic layer was dried over Mg2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give light yellow oil
  8. customThe crude product was purified by column chromatography (eluent: 5% ethyl acetate in hexane to 20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-dc357bbe34844dba9316f46f684ae9b7
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173939B2

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