Acetic Anhydride → Ralaniten Acetate

HRID 705323노트

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HRID 705323 반응식
[Cl:1][CH2:2][C@@H:3]([OH:27])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:15]2[CH:26]=[CH:25][C:18]([O:19][CH2:20][C@H:21]([OH:24])[CH2:22][OH:23])=[CH:17][CH:16]=2)([CH3:14])[CH3:13])=[CH:8][CH:7]=1.C(O[C:32](=[O:34])[CH3:33])(=O)C>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:4]([O:23][CH2:22][C@@H:21]([O:24][C:32](=[O:34])[CH3:33])[CH2:20][O:19][C:18]1[CH:17]=[CH:16][C:15]([C:12]([C:9]2[CH:8]=[CH:7][C:6]([O:5][CH2:4][C@H:3]([O:27][C:18](=[O:19])[CH3:17])[CH2:2][Cl:1])=[CH:11][CH:10]=2)([CH3:14])[CH3:13])=[CH:26][CH:25]=1)(=[O:5])[CH3:3]

참가 물질

5

반응물 2

HCID 7918Acetic AnhydrideHCID 45107537Ralaniten

생성물 1

HCID 86278934Ralaniten Acetate수율 187.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

To a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (500 mg, 1.27 mmol) in anhydrous pyridine (6.0 mL) were successively added acetic anhydride (605 μL, 6.35 mmol) and a catalytic amount of DMAP. After 14 h, the reaction mixture was quenched with an aqueous solution of sodium chloride and stirred for 15 min, and the resulting mixture was extracted twice with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulfate, and filtered. Solvents were evaporated, and the resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane) to provide the title compound (621 mg, 94%) as a sticky solid.

후처리

  1. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  2. extractionthe resulting mixture was extracted twice with dichloromethane
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customSolvents were evaporated
  6. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-0b2fa4be27b846afb3ef253c116499be
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09173939B2

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