تفاعل #2446129

معادلة التفاعل

HCl

L-cysteine hydrochloride hydrate

KOH

KBr

5-chloromethyl-8-hydroxyquinoline hydrochloride

→

S-(8-hydroxyquinolin-5-ylmethyl)-L-cysteine

المذيبات

H2O

DMSO

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe suspension was stirred at room temperature 12 h
3. 3
   غسيلThe precipitate was washed with water and acetone
4. 4
   أخرىThe crude product was further purified by semi-preparative HPLC
5. 5
   أخرىto yield compound M12

الإجراء التجريبي

L-cysteine hydrochloride hydrate (37 mg, 0.31 mmol) was dissolved in DMSO (3 ml). To the solution powdered KOH (36 mg, 0.34 mmol) was added, and the mixture was stirred for 30 min at room temperature. Then, powdered 5-chloromethyl-8-hydroxyquinoline hydrochloride (A2) (65 mg, 0.34 mmol) was added. The suspension was stirred at room temperature 12 h, 2 N HCl was added and the pH was adjusted to 5. The precipitate was washed with water and acetone. The crude product was further purified by semi-preparative HPLC to yield compound M12: 53 mg (61%). HPLC (tR): 38.1 min (linear gradient: 50% B for the first 4 min, increased linearly to 100% B for 60 min) [α]D20=20.5° (c=1.0, H2O); 1H NMR (250 MHz, D2O) 2.89 (d, J=5.6 Hz, 2H), 3.95 (dd, J=5.1, 5.0 Hz, 1H), 4.18 (s, 2H), 7.25 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.96 (dd, J=8.7, 5.5 Hz, 1H), 8.88 (d, J=5.4 Hz, 1H), 9.22 (d, J=8.7 Hz, 1H); IR (KBr) cm−1: 3438 (broad), 3081, 1685, 1637, 1560; Mass spectrometry: calculated for C12H12N2O3 m/z [M+H]+=279.33. found [M+H]+=279.13.

المصدر