Sodium Azide → (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane

HRID 2407867Notes

Reaction equation

CS(O[C@@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>CN(C=O)C>[N:34]([C@H:6]([CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+:35]=[N-:36]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-yl methanesulfonate (1 eq) and NaN3 (5 eq) in DMF (0.5 M) was stirred at 100° C. over night. The reaction mixture was filtered and washed with DCM. The filtrate was concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-15% EtOAc/Hex to give (R)-(2-azido-3-(hexadecyloxy)propoxy)(tert-butyl)dimethylsilane as acolorless oil.

Workup

filtrationThe reaction mixture was filtered
washwashed with DCM
concentrationThe filtrate was concentrated en vaccuo
customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record: ord-5f086ede24314a2f9cb2da820c72c744
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08808703B2

Reaction notes

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