تفاعل #66024

معادلة التفاعل

NMM

Compound 5a

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

NH2OH.HCl

KOH

→

product

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

المذيبات

THF

MeOH

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred at 0° C. for 30 min
2. 2
   ترشيحThe 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
   ترشيحThe reaction mixture was filtered
6. 6
   أخرىthe solvent evaporated
7. 7
   workup.DISSOLUTIONthe residue dissolved in H2O (25 mL)
8. 8
   استخلاصthe aqueous layer was extracted with EtOAc (3×30 mL)
9. 9
   تجفيفThe combined organic layers were dried over MgSO4
10. 10
    أخرىevaporated in vacuo

الإجراء التجريبي

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.

المصدر