Lithium azide → 1-Azido-2-(2-benzoyloxypropan-1-yl)-3-hexadecylthiopropane

HRID 847019Notes

Reaction equation

HRID 847019 reaction equation
CS(O[CH2:6][CH:7]([CH2:26][CH:27]([O:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:28])[CH2:8][S: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][CH2:24][CH3:25])(=O)=O.[N-:38]=[N+:39]=[N-:40].[Li+].N(CC(NC(OC(C)(C)C)=O)CSCCCCCCCCCCCCCCCC)=[N+]=[N-]>CN(C)C=O>[N:38]([CH2:6][CH:7]([CH2:26][CH:27]([O:29][C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:28])[CH2:8][S: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][CH2:24][CH3:25])=[N+:39]=[N-:40]

Participants

5

Reactant 3

HCID 88163Lithium azideHCID 148350953-Azido-2-tert-butoxycarbonylamino-1-hexadecylthiopropaneHCID 536352672-(2-Benzoyloxypropan-1-yl)-3-hexadecylthiopropanol methanesulfonate

Product 1

HCID 198841951-Azido-2-(2-benzoyloxypropan-1-yl)-3-hexadecylthiopropaneYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the previously obtained 2-(2-benzoyloxypropan-1-yl)-3-n-hexadecylthiopropyl methanesulfonate m12a and 1.297 g (26.5 mM) of lithium azide in 50 ml of dimethylformamide is allowed to react by the same procedure as described in (53) and 1.291 g (96.6% yield) of the titled compound m12b is obtained.

Workup

  1. customto react by the same procedure

Sources & evidence

ORD record
ord-2830154dfc284b2190328ccf55019e08
Source dataset
uspto-grants-1992_08
Patent number
US05138067

Reaction notes

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