反応 #66026

反応方程式

{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

溶媒

THF

MeOH

反応条件

後処理

1. 1
   workup.STIRRINGstirred at 0° C. for 30 min
2. 2
   ろ過The 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
   ろ過The reaction mixture was filtered
6. 6
   その他the solvent evaporated
7. 7
   workup.DISSOLUTIONthe residue dissolved in H2O (20 mL)
8. 8
   抽出the aqueous layer was extracted with EtOAc (3×30 mL)
9. 9
   乾燥The combined organic layers were dried over MgSO4
10. 10
    その他evaporated in vacuo

実験手順

{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.

出典