1-Butanaminium, N,N,N-tributyl-, azide → HCID 118005663, compound

HRID 1488291Notes

Reaction equation

HRID 1488291 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][C@H:9]1[O:38][C@H:37]([CH2:39][O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@@H:28]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:10]1[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=O)=O.[N-:48]=[N+:49]=[N-:50].C([N+](CCCC)(CCCC)CCCC)CCC>C(C#N)(C)=O>[CH2:12]([O:11][C@@H:10]1[C@@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:28]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@@H:37]([CH2:39][O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[O:38][C@@H:9]1[CH2:8][CH2:7][CH2:6][N:48]=[N+:49]=[N-:50])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 118005599HCID 118005599, compound

Product 1

HCID 118005663HCID 118005663, compound

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)propyl methanesulfonate (3.78 g, 5.72 mmol) in AcCN (50 mL) was added tetrabutylammonium azide (1.66 g, 5.83 mmol). The resulting mixture allowed to reflux overnight. After cooled to rt, the reaction mixture was concentrated. The residue was dissolved in ether (50 mL), which was washed with water (2×50 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (120 g, eluting with 0-30% EtOAc in hexanes) to give the title compound. 1H NMR (CDCl3) δ 1.58-1.68 (m, 2H), 1.74-1.86 (m, 2H), 3.32-3.41 (m, 2H), 3.58-3.76 (m, 4H), 3.76-3.85 (m, 2H), 4.40 (m, 1H), 4.52 (t, J=10.4, 2H), 4.65 (dd, J=11.7, 2.5, 2H), 4.75 (d, J=11.7, 1H), 4.86 (m, 2H), 4.97 (d, J=10.8, 1H), 7.16 (m, 2H), 7.28-7.40 (m, 18H).

Workup

  1. temperatureto reflux overnight
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionThe residue was dissolved in ether (50 mL)
  4. washwhich was washed with water (2×50 mL), brine (25 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography on silica gel (120 g, eluting with 0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0ad1bf8bda8d45e2ad506c25a2b3e73b
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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