Water → HCID 67360703, compound

HRID 2065678Notes

Reaction equation

HRID 2065678 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.BrC1C=CC(Cl)=NC=1.O>CS(C)=O>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]([O:17][C:14]2[CH:13]=[CH:12][C:11]([CH2:10][C@H:9]([NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])[C:18]([OH:20])=[O:19])=[CH:16][CH:15]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 691404-ChloroquinolineHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-HCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 67360703HCID 67360703, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-Boc-L-Tyrosine (0.844 g, 3 mmol) and KOBu-t (0.727 g, 6.5 mmol) are dissolved in dry DMSO (2.9 mL) under argon atmosphere in a tightly closed glass reaction tube and stirred for 15 min, then 4-chloroquinoline (0.491 g, 3 mmol) is added. The mixture is stirred for 6 days at 30° C. When only traces of 5-bromo-2-chloropyridine are detected (LC-MS control), the reaction mixture is poured into water (40 mL) and the aqueous phase is washed with diethyl ether (2×20 mL). The pH of aqueous phase is adjusted to ˜4 by adding 20% aqueous citric acid. The product precipitated is collected on filter and washed with water (50 mL) to give the title compound (0.833 g, 68%) as a grey solid.

Workup

  1. stirringThe mixture is stirred for 6 days at 30° C
  2. washthe aqueous phase is washed with diethyl ether (2×20 mL)
  3. additionby adding 20% aqueous citric acid
  4. customThe product precipitated
  5. customis collected
  6. filtrationon filter
  7. washwashed with water (50 mL)

Sources & evidence

ORD record
ord-75116f91ed8b447c867128410650ddb5
Source dataset
uspto-grants-2012_10
Patent number
US08288549B2

Reaction notes

Loading…