1-Butanaminium, N,N,N-tributyl-, azide → HCID 118411333, compound

HRID 708332Notes

Reaction equation

HRID 708332 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22]I.[N-:30]=[N+:31]=[N-:32].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[N:30]([CH2:22][C@@H:7]1[C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9](=[O:10])[N:6]1[CH2:5][C:4]1[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:3]=1[O:2][CH3:1])=[N+:31]=[N-:32]

Participants

4

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 118411332HCID 118411332, compound

Product 1

HCID 118411333HCID 118411333, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of benzyl ((2S,3S)-1-(2,4-dimethoxybenzyl)-2-(iodomethyl)-4-oxoazetidin-3-yl)carbamate (5.00 g, 9.80 mmol) in THF (100 mL) at 0° C. was added TEA (2.73 g, 19.6 mmol) followed by a solution of tetrabutylammonium azide (3.62 g, 12.7 mmol) in THF. After stirring at rt for 16 h, it was filtered and concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 2%), affording the title compound (3.4 g, 81%) as a white solid.

Workup

  1. filtrationit was filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 2%)

Sources & evidence

ORD record
ord-21a68544e38c4be4831b75f2e64f7e46
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

Loading…