Réaction #66026

Équation de réaction

{Carboxymethyl-[4-(4-bromo-phenoxy)-benzenesulphonyl]-amino}-acetic acid

{[4-(4-Bromophenoxy)-benzenesulphonyl]-tert-butoxycarbonylmethyl-amino}-aceticacid tert-butyl ester

NMM

NH2OH

HCl

KOH

→

product

{[4-(4-Bromo-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 (20 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

{Carboxymethyl-[4-(4-bromo-phenoxy)-benzenesulphonyl]-amino}-acetic acid (4d) (1.90 g, 4.30 mmol) was dissolved in dry THF (50 mL). ECF (0.35 mL, 3.70 mmol), and NMM (0.40 mL, 3.70 mmol) were added and stirred for 40 min at 0° C. NH2OH×HCl (0.30 g, 4.30 mmol) and KOH (0.24 g, 4.30 mmol) were dissolved in dry MeOH (20 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 (20 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 and evaporated in vacuo to yield the pure product as white crystals. Yield: 1.80 g, 3.90 mmol, 91%. 1H NMR (D2O): δ 7.7 (d, J=8.2 Hz, 2H, ArH), 7.5 (d, J=8.8 Hz, 2H, ArH), 7.0 (d, J=8.8 Hz, 2H, ArH), 4.0 (s, 4H, CH2COOH). ESI-MS calcd for C16H15BrN2O7S 457.98 [M-H]−, obsd 459.27.

Source