Hydrochloric Acid → S-(8-hydroxyquinolin-5-ylmethyl)-L-cysteine

HRID 557252

Reaction equation

HRID 557252 reaction equation
O.Cl.[NH2:3][C@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].[OH-].[K+].Cl.Cl[CH2:14][C:15]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]=[N:20]2.Cl.[K+].[Br-]>CS(C)=O.O>[OH:25][C:22]1[CH:23]=[CH:24][C:15]([CH2:14][S:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[NH2:3])=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[CH:17]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 23462L-Cysteine hydrochloride monohydrateHCID 253877Potassium BromideHCID 122695968-Quinolinol, 5-(chloromethyl)-, hydrochloride (1:1)

Product 1

HCID 10062096S-(8-hydroxyquinolin-5-ylmethyl)-L-cysteine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

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.

Workup

  1. additionwas added
  2. stirringThe suspension was stirred at room temperature 12 h
  3. washThe precipitate was washed with water and acetone
  4. customThe crude product was further purified by semi-preparative HPLC
  5. customto yield compound M12

Sources & evidence

ORD record
ord-f895bd258ecf4ea5ba4ec27e3dd851f8
Source dataset
uspto-grants-2011_11
Patent number
US08058442B2

Linked notes

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