Acetic Anhydride → Ralaniten Acetate

HRID 705323Notes

Reaction equation

HRID 705323 reaction equation
[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]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 45107537Ralaniten

Product 1

HCID 86278934Ralaniten AcetateYield 187.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-0b2fa4be27b846afb3ef253c116499be
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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