Réaction #66024

Équation de réaction

NMM

Compound 5a

{[4-Phenoxy-benzenesulphonyl]-carboxymethyl-amino}-acetic acid

NH2OH.HCl

KOH

→

product

{[4-Phenoxy-benzenesulphonyl]-hydroxycarbamoylmethyl-amino}-acetic acid

Solvants

THF

MeOH

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred at 0° C. for 30 min
2. 2
   FiltrationThe solids were filtered off
3. 3
   workup.ADDITIONthe THF solution was added dropwise to the methanol filtrate
4. 4
   workup.STIRRINGstirred for 2 h at 0° C
5. 5
   FiltrationThe reaction mixture was filtered
6. 6
   Autrethe solvent evaporated
7. 7
   workup.DISSOLUTIONthe residue dissolved in H2O (25 mL)
8. 8
   Extractionthe aqueous layer was extracted with EtOAc (3×30 mL)
9. 9
   SéchageThe combined organic layers were dried over MgSO4
10. 10
    Autreevaporated in vacuo

Mode opératoire

Compound 5a (711 mg, 1.95 mmol) was dissolved in dry THF (5 mL). ECF (160 μL, 1.95 mmol), and NMM (180 μL, 1.95 mmol) were added and this mixture was stirred for 40 min at 0° C. NH2OH.HCl (136 mg, 1.95 mmol) and KOH (109 mg, 1.95 mmol) were dissolved in dry MeOH (5 mL) and stirred at 0° C. for 30 min. The solids were filtered off, and the THF solution was added dropwise to the methanol filtrate and stirred for 2 h at 0° C. The reaction mixture was filtered, the solvent evaporated, and the residue dissolved in H2O (25 mL). After adjusting the pH to 1-2, the aqueous layer was extracted with EtOAc (3×30 mL). The combined organic layers were dried over MgSO4, evaporated in vacuo, and co-evaporated with EtOAc (3×3 mL) to yield the pure product as light-pink solid. Yield: 565 mg, 1.10 mmol, 56%. 1H-NMR (DMSO-d6): δ 7.87 (d, 2H, 2JHH=9.0 Hz, ArH), 7.42 (d, 2H, 2JHH=9.0 Hz, ArH), 7.35 (s, 2H, ArH), 6.98 (d, 1H, 3JHH=9.0 Hz, ArH), 6.90 (d, 2H, 3JHH=9.0 Hz, ArH), 4.07 (s, 2H, 2×CH2CO2H), 3.85 (s, 2H, 2×CH2CONHOH). ESI-MS calcd for C16H16N2O7S 380.07 [M-H]−, obsd 381.1.

Source