Succinic anhydride → (S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol trisuccinate

HRID 705327Notes

Reaction equation

HRID 705327 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:28]1(=[O:34])[O:33][C:31](=[O:32])[CH2:30][CH2:29]1>N1C=CC=CC=1>[C:28]([OH:33])(=[O:34])[CH2:29][CH2:30][C:31]([OH:5])=[O:32].[C:28]([OH:33])(=[O:34])[CH2:29][CH2:30][C:31]([OH:5])=[O:32].[C:28]([OH:33])(=[O:34])[CH2:29][CH2:30][C:31]([OH:5])=[O:32].[Cl:1][CH2:2][C@@H:3]([OH:27])[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([C:15]2[CH:16]=[CH:17][C:18]([O:19][CH2:20][C@@H:21]([OH:24])[CH2:22][OH:23])=[CH:25][CH:26]=2)([CH3:14])[CH3:13])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 45107537Ralaniten

Product 1

HCID 131733683(S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol trisuccinate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (700 mg, 1.77 mmol) in anhydrous pyridine (6.0 ml) were added succinic anhydride (710 mg, 7.10 mmol) and the mixture was heated at 70° C. After 3 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 ethyl acetate. 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: 5% to 30% methanol in dichloromethane) to provide the title compound.

Workup

  1. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  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: 5% to 30% methanol in dichloromethane)

Sources & evidence

ORD record
ord-fdd9599908bc422aa636f6d296deaa92
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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