Triethylamine → HCID 85064038, compound

HRID 226136Notes

Reaction equation

HRID 226136 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][S:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]([OH:21])=O)[CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9].C(OC(Cl)=O)C.C(N(CC)CC)C.[OH-:35].[K+].Cl.[NH2:38]O>O1CCCC1.CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][S:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]([NH:38][OH:35])=[O:21])[CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 67019525HCID 67019525, compound

Product 1

HCID 85064038HCID 85064038, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{3-[(furan-2-ylmethyl)-sulfamoyl]-phenyl}-acrylic acid (5z) (0.17 g, 0.55 mmol) in tetrahydrofuran (2.0 ml) at 0° C. temperature ethylchloroformate (0.072 g 0.66 mmol) and triethylamine (0.1 ml, 0.72 mmol) were added and the resulting mixture was stirred for 15 min. To a stirred solution of KOH (0.058 g, 1.04 mmol) in methanol (0.25 ml) a solution of hydroxylamine hydrochloride (0.072 g, 1.04 mmol) in methanol (0.7 ml) was added at 0° C. The mixture was stirred for 15 min., the precipitated KCl was removed and the filtrate was added to the first solution. The reaction mixture was stirred at room temperature for 2 hours. Then the mixture was partitioned between 1N KH2PO4 solution and ethyl acetate. The organic layer was washed with water, saturated NaCl, and dried (Na2SO4). The solvent was evaporated and the residue was washed successively with dichloromethane and ethyl acetate affording the title compound (0.057 g, 32%), M.p. 165° C., 1H NMR (DMSO-d6, HMDSO) δ: 4.03 (2H, d, J=6.4 Hz); 6.23 (2H, m); 6.54 (1H, d, J=16.0 Hz); 7.38-8.05 (6H, m); 8.20 (1H, t, J=6.4 Hz); 9.09 (1H, br s); 10.83 (1H, br s). HPLC analysis on Zorbax SB-C18 column: impurities 8% (column size 4.6×150 mm; mobile phase methanol—0.1% H3PO4, gradient from 30 to 90%; detector UV 270 nm; flow rate 1.5 ml/min; sample concentration 1.0 mg/ml). Anal. Calcd for C14H14N2O5S, %: C 52.17, H 4.38, N 8.69. Found, %: C 51.87, H 4.39, N 8.41.

Workup

  1. stirringThe mixture was stirred for 15 min.
  2. customthe precipitated KCl was removed
  3. additionthe filtrate was added to the first solution
  4. stirringThe reaction mixture was stirred at room temperature for 2 hours
  5. customThen the mixture was partitioned between 1N KH2PO4 solution and ethyl acetate
  6. washThe organic layer was washed with water, saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated
  9. washthe residue was washed successively with dichloromethane and ethyl acetate affording the title compound (0.057 g, 32%), M.p. 165° C., 1H NMR (DMSO-d6, HMDSO) δ: 4.03 (2H, d, J=6.4 Hz); 6.23 (2H, m); 6.54 (1H, d, J=16.0 Hz); 7.38-8.05 (6H, m); 8.20 (1H, t, J=6.4 Hz); 9.09 (1H, br s); 10.83 (1H, br s)

Sources & evidence

ORD record
ord-f95a8427cacb4fa1b561e9144a20767e
Source dataset
uspto-grants-2009_07
Patent number
US07557140B2

Reaction notes

Loading…