Furosemide → HCID 58979751, compound

HRID 1180618Notes

Reaction equation

HRID 1180618 reaction equation
[CH:1]1[CH:2]=[C:3]([CH2:6][NH:7][C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:10]([Cl:21])[CH:9]=2)[O:4][CH:5]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CC(C)=O>[Cl:21][C:10]1[CH:9]=[C:8]([NH:7][CH2:6][C:3]2[O:4][CH:5]=[CH:1][CH:2]=2)[C:13]([C:14]([O:16][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:15])=[CH:12][C:11]=1[S:17](=[O:19])(=[O:18])[NH2:20]

Participants

5

Reactant 3

HCID 3440FurosemideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 58979751HCID 58979751, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of furosemide (ONBIO Inc., 20 g, 60.5 mmol), K2CO3 (8.3 g, 60.5 mmol) and ethyl bromoacetate (10.1 g, 6.7 mL, 60.5 mmol) in dry acetone (400 mL) was stirred at room temperature for 16 hours. The solvent was evaporated at reduced pressure. The residue was diluted with CH2Cl2, the solid K2CO3 was removed by filtration. The filtrate was washed with water, brine and dried over Na2SO4. The residue obtained after evaporation of the solvent was dried under vacuum to give the title compound (23.5 g, 93% yield) as a white foam. Mp 46° C. 1H NMR (300 MHz, d6-DMSO) δ 8.48 (s, 1H), 8.37 (br t, J=5.6 Hz, 1H), 7.62 (s, 1H), 7.39 (br s, 2H), 7.14 (s, 1H), 6.37-6.43 (m, 2H), 4.93 (s, 2H), 4.62 (br d, J=5.7 Hz, 2H), 4.17 (q, J=7.0 Hz, 2H), 1.19 (br t, J=14.1 Hz, 3H). 13C NMR (75 MHz, d6-DMSO) δ 167.6, 165.8, 152.2, 151.1, 142.8, 137.0, 133.0, 127.1, 114.1, 110.5, 107.7, 106.3, 61.2, 61.0, 14.0. Mass spectrum (API-TIS) m/z 417 (MH+), 434 (MNH4+). Anal. calcd for C16H17ClN2O7S: C, 46.10; H, 4.11; N, 6.72. Found: C, 46.13; H, 3.97; N, 6.47.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. additionThe residue was diluted with CH2Cl2
  3. customthe solid K2CO3 was removed by filtration
  4. washThe filtrate was washed with water, brine
  5. dry with materialdried over Na2SO4
  6. customThe residue obtained
  7. customafter evaporation of the solvent
  8. customwas dried under vacuum

Sources & evidence

ORD record
ord-cc50050b499c49ae9fc80ef3918de582
Source dataset
uspto-grants-2007_10
Patent number
US07282519B2

Reaction notes

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