Reaktion #586066

Reaktionsgleichung

HCl

product

3-Chloro-1-methyl-5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid ethyl ester

LiOH

→

title compound

3-Chloro-1-methyl-5-[(4′-trifluoromethyl-biphenyl-2-carbonyl)-amino]-1H-indole-2-carboxylic acid

Lösungsmittel

methanol

water

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe aqueous layer was extracted with EtOAc (250 mL)
2. 2
   WaschenThe organic layer was washed with brine (200 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   SonstigeThe solvent was evaporated in vacuo
5. 5
   Sonstigeto give the crude product which
6. 6
   Sonstigewas purified by recrystallization from 1:1 EtOAc/ether

Vorschrift

The product of step (d) may be hydrolyzed as follows: the compound (5.51 g) was dissolved in THF (120 mL) and methanol (40 mL). Under stirring conditions was added LiOH (1.32 g) in water (40 mL). The reaction mixture was stirred at room temperature overnight. To the reaction mixture was then added 1 N HCl solution (60 mL), and the aqueous layer was extracted with EtOAc (250 mL). The organic layer was washed with brine (200 mL), and dried (MgSO4). The solvent was evaporated in vacuo to give the crude product which was purified by recrystallization from 1:1 EtOAc/ether to afford 4.4 g of the title compound.

Quelle