Acetic Anhydride → Ralaniten Acetate

HRID 705324Notes

Reaction equation

HRID 705324 reaction equation
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]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 45107537Ralaniten

Product 1

HCID 86278934Ralaniten AcetateYield 182.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dc357bbe34844dba9316f46f684ae9b7
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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