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

HRID 2358947

反応式

HRID 2358947 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ce49a376d29f4b5f8a94d2aa5580e70f
出典データセット
uspto-grants-2014_04
特許番号
US08685955B2

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