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Pyridine → (R)-2-azido-3-(hexadecyloxy)propyl trifluoromethanesulfonate

HRID 2407869
Notes
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Reaction equation

HRID 2407869 reaction equation
[N:1]([C@H:4]([CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][OH:6])=[N+:2]=[N-:3].N1C=CC=CC=1.[O:31](S(C(F)(F)F)(=O)=O)[S:32]([C:35]([F:38])([F:37])[F:36])(=O)=[O:33]>C(Cl)Cl>[F:36][C:35]([F:38])([F:37])[S:32]([O:6][CH2:5][C@H:4]([N:1]=[N+:2]=[N-:3])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])(=[O:33])=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 86678274(S)-2-azido-3-(hexadecyloxy)propan-1-ol

Product 1

HCID 86678276(R)-2-azido-3-(hexadecyloxy)propyl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-azido-3-(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-azido-3-(hexadecyloxy)propyl trifluoromethanesulfonate.

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-bf7954df9359464c82ab28f081eb86c6
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08808703B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes