Tris(hydroxymethyl)aminomethane → HCID 58215565, compound

HRID 593597Notes

Reaction equation

HRID 593597 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:17][N:18]([CH3:23])[S:19](Cl)(=[O:21])=[O:20].C(O)C(N)(CO)CO>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([O:8][S:19](=[O:21])(=[O:20])[N:18]([CH3:23])[CH3:17])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 62657Potassium Phosphate, TribasicHCID 83372Dimethylsulphamoyl chlorideHCID 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 58215565HCID 58215565, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

A flask is charged with 5-bromo-pyridin-3-ol (0.200 g, 1.126 mmol), potassium phosphate (0.631 g, 2.884 mmol) and acetone (5 mL) and cooled to 0° C. Dimethylsulfamoyl chloride (0.261 g, 1.802 mmol) is then added dropwise and the cooling bath is removed. After 2 h, the mixture is diluted with acetone, filtered and the filtrate is concentrated in vacuo. The residue is dissolved in THF (30 mL) and polymer-supported trisamine (3.85 mmol/g, 0.7 g, 2.7 mmol) is added. After 1 h, the mixture is filtered. Concentration in vacuo gives a residue which is purified by silica gel flash chromatography (heptane-ethyl acetate, 9:1 to 4:1) to give dimethyl-sulfamic acid 5-bromo-pyridin-3-yl ester as a solid. 1H NMR (400 MHz, CDCl3) δ ppm 3.05 (s, 3H), 7.86 (m, 1H), 8.50 (d, J=2.3 Hz, 1H), 8.62 (d, J=1.9 Hz, 1H).

Workup

  1. customthe cooling bath is removed
  2. additionthe mixture is diluted with acetone
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in THF (30 mL)
  6. waitAfter 1 h
  7. filtrationthe mixture is filtered
  8. concentrationConcentration in vacuo
  9. customgives a residue which
  10. customis purified by silica gel flash chromatography (heptane-ethyl acetate, 9:1 to 4:1)

Sources & evidence

ORD record
ord-2c555f03c8414fb4b4e345c9f60347ff
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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