Tris(hydroxymethyl)aminomethane → HCID 58215565, compound

HRID 1661642Notes

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

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

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

Sources & evidence

ORD record: ord-56eca305629340c39bb3de0fbb740073
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030334B2

Reaction notes

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