L-Leucinol → HCID 178472053, compound

HRID 1047155Notes

Reaction equation

HRID 1047155 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9](/[C:11](=[CH:17]/OCC)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:21][C@@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:9](/[C:11](=[CH:17]/[NH:21][C@@H:22]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH2:23][OH:24])/[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:10])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 111307L-LeucinolHCID 86665042HCID 86665042, compound2×

Product 1

HCID 178472053HCID 178472053, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude ethyl (2Z)-2-[5-bromo-2-chloropyridin-3-yl)carbonyl]-3-ethoxyprop-2-enoate (Intermediate 13, 3.2 g) was dissolved in dichloromethane (30 mL) and (2S)-2-amino-4-methylpentan-1-ol (2.17 g, 14.7 mmol) was added. The mixture was stirred for 30 min at room temperature. Dichloromethane (70 mL) was added to the reaction mixture and the mixture was washed with water (2×100 mL). The organic layer was dried over anhydrous sodium sulphate, filtered and concentrated under reduced pressure to give a thick mass which was purified by flash column chromatography. The product was eluted with the gradient of 20% ethyl acetate/petroleum ether to afford colorless thick mass 2.5 g (80%) of ethyl (2Z)-2-[(5-bromo-2-chloropyridin-3-yl)carbonyl]-3-{[(2S)-1-hydroxy-4-methylpentan-2-yl]amino}prop-2-enoate.

Workup

  1. washthe mixture was washed with water (2×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a thick mass which
  6. customwas purified by flash column chromatography
  7. washThe product was eluted with the gradient of 20% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-59fd923fde274d6db227fc0d38610c98
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

Loading…