تفاعل #657344

معادلة التفاعل

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

NaOH

→

title compound

المردود 89.0%

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

المردود 89.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىat RT
2. 2
   درجة الحرارةbefore being cooled down
3. 3
   أخرىquenched with 1N HCl (136 mL)
4. 4
   أخرىTHF was removed under reduced pressure
5. 5
   استخلاصthe aqueous layer was extracted with DCM
6. 6
   تجفيفThe combined organic layers were dried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   أخرىThe crude solid was recrystallised in CH3CN

الإجراء التجريبي

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 Intermediate 2) (28 g, 68 mmol) in THF (450 mL) at RT was added 1N NaOH (136 mL, 136 mmol). The reaction mixture was stirred at this temperature for 5 h before being cooled down and quenched with 1N HCl (136 mL). THF was removed under reduced pressure and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude solid was recrystallised in CH3CN to give the title compound (23.9 g, 89% yield) as a pale yellow powder. 1H NMR (300 MHz, CDCl3) δ7.55-7.48 (m, 2H), 7.41 (d, J=8.9 Hz, 1H), 7.38-7.31 (m, 2H), 7.22 (dd, J=2.9 and 8.9 Hz, 1H), 6.90 (d, J=2.9 Hz, 1H), 4.59 (dd, J=6.9 and 6.9 Hz, 1H), 3.81 (s, 3H), 3.70 (dd, J=6.9 and 25.7 Hz, 1H), 3.61 (dd, J=6.9 and 25.7 Hz, 1H), 2.63 (s, 3H). LC/MS: m/z 397 [M(35Cl)+H]+, Rt 2.11 min.

المصدر