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

HRID 2204973Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-98c72d14ce5b4f62a03886d6375f5f3f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365506B2

Reaction notes

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