Reaktion #220586

Reaktionsgleichung

K2CO3

2-(4-Bromo-benzenesulfonylamino)-3-methyl-butyric acid methyl ester

4-hydroxymethyl phenyl boronic acid

→

2-(4′-Hydroxymethyl-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester

Ausbeute 67.0%

Lösungsmittel

H2O

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheat
2. 2
   Temperaturto reflux overnight
3. 3
   SonstigeAfter TLC confirmation of reaction completion, solvent
4. 4
   Sonstigewas removed by rotovap, residue
5. 5
   Sonstigepartitioned between EtOAc and brine, organic layer
6. 6
   Trocknendried over MgSO4, solvent
7. 7
   Sonstigeremoved
8. 8
   Sonstigecrude residue was triturated with EtOAc

Vorschrift

Step 1B [Intermediate 2: 2-(4-Bromo-benzenesulfonylamino)-3-methyl-butyric acid methyl ester (3.4 g, 9.71 mmol), 4-hydroxymethyl phenyl boronic acid (1.48 g, 9.71 mmol, 1 equiv.), Pd(PPh3)4 (561 mg, 0.48 mmol, 0.05 equiv.) were dissolved in ethylene glycol dimethyl ether (90 mL) under N2 atmosphere and stirred at room temperature for 30 min. Then K2CO3 (2.68 g, 19.4 mmol, 2 equiv.) in H2O (30 mL) was introduced to the reaction mixture and heat to reflux overnight. After TLC confirmation of reaction completion, solvent was removed by rotovap, residue partitioned between EtOAc and brine, organic layer dried over MgSO4, solvent removed, crude residue was triturated with EtOAc to give 2-(4′-Hydroxymethyl-biphenyl-4-sulfonylamino)-3-methyl-butyric acid methyl ester in 67% yield (2.46 g).

Quelle