Reaction #2446129

Reaction equation

HCl

L-cysteine hydrochloride hydrate

KOH

KBr

5-chloromethyl-8-hydroxyquinoline hydrochloride

→

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

Solvents

H2O

DMSO

Conditions

Workup

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

Procedure

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.

Source