Reaction #169200

Reaction equation

methyl [(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetate

sodium hydroxide

→

title compound

Yield 98.0%

[(4S)-6-(4-Chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetic acid

Yield 98.0%

Solvents

THF

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Otherbefore being quenched with 1N HCl (36.2 ml)
3. 3
   Concentrationconcentrated in vacuo
4. 4
   workup.ADDITIONWater is then added
5. 5
   Extractionthe aqueous layer was extracted with DCM (×3)
6. 6
   Dryingthe combined organic layers were dried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure

Procedure

To a solution of methyl [(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetate (for a preparation see Reference compound G) (7.4 g, 18.1 mmol) in THF (130 ml) at room temperature was added 1N sodium hydroxide (36.2 ml, 36.2 mmol). The reaction mixture was stirred at this temperature for 5 h before being quenched with 1N HCl (36.2 ml) and concentrated in vacuo. Water is then added and the aqueous layer was extracted with DCM (×3) and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (7 g, 98% yield) as a pale yellow solid.

Source