Pyridine → (R)-2,3-bis(hexadecyloxy)propyl trifluoromethanesulfonate

HRID 2204965Notes

Reaction equation

HRID 2204965 reaction equation
[CH2:1]([O:17][C@H:18]([CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:19][OH:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].N1C=CC=CC=1.[O:45](S(C(F)(F)F)(=O)=O)[S:46]([C:49]([F:52])([F:51])[F:50])(=O)=[O:47]>C(Cl)Cl>[F:50][C:49]([F:52])([F:51])[S:46]([O:20][CH2:19][C@H:18]([O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])(=[O:47])=[O:45]

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10414934(S)-2,3-Bis(hexadecyloxy)propan-1-ol

Product 1

HCID 86678269(R)-2,3-bis(hexadecyloxy)propyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2,3-bis(hexadecyloxy)propan-1-ol (1 eq) and pyridine (4 eq) in DCM (0.1 M) at 0° C., was added Tf2O (2 eq). The reaction was stirred at 0° C. for 1 hour and quenched by H2O. The aqueous phase was extracted with DCM. The combined organic phases were washed with H2O, and the aqueous phase was back extracted with DCM. The combined organic phases were washed with saturated NaHCO3 and brine, dried over anhydrous Na2SO4 and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-10% EtOAc/Hex to give (R)-2,3-bis(hexadecyloxy)propyl trifluoromethanesulfonate as a colorless oil.

Workup

  1. customquenched by H2O
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe combined organic phases were washed with H2O
  4. extractionthe aqueous phase was back extracted with DCM
  5. washThe combined organic phases were washed with saturated NaHCO3 and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated en vaccuo
  8. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-b70a83e80c604dfc9b47f3bc233c57e4
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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