Acetyl chloride → (S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)-2-hydroxypropyl acetate

HRID 705319Notes

Reaction equation

HRID 705319 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.N1C(C)=CC=CC=1C.[C:36](Cl)(=[O:38])[CH3:37]>ClCCl>[C:36]([O:23][CH2:22][C@@H:21]([OH:24])[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]([OH:27])[CH2:2][Cl:1])=[CH:11][CH:10]=2)([CH3:14])[CH3:13])=[CH:26][CH:25]=1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 79372,6-LutidineHCID 45107537Ralaniten

Product 1

HCID 86292878(S)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)-2-hydroxypropyl acetateYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-(4-(2-(4-((S)-3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol (1000 mg, 2.53 mmol) in anhydrous dichloromethane (8.0 mL) at −78° C. were successively added 2,6-lutidine (590 μL, 5.06 mmol) and acetic chloride (144 μL, 2.02 mmol) dropwise. After 1 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 (300 mg, 27%) as a sticky solid.

Workup

  1. customat −78° C.
  2. customthe reaction mixture was quenched with an aqueous solution of sodium chloride
  3. extractionthe resulting mixture was extracted twice with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customSolvents were evaporated
  7. customthe resulting crude material was purified by silica gel flash chromatography (eluent: 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-2c119ae4179649c99a9bb0e920fe3751
Source dataset
uspto-grants-2015_11
Patent number
US09173939B2

Reaction notes

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