Methanol → HCID 86663862, compound

HRID 1022659Notes

Reaction equation

HRID 1022659 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[O:11][CH:10]2[C:12]([OH:14])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:15]([NH:22][CH2:23][CH2:24][OH:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CO.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C1COCC1>[CH2:15]([N:22]([CH2:23][CH2:24][OH:25])[C:12]([CH:10]1[CH:9]([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:11]1)=[O:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 4348BenzylethanolamineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 86663861HCID 86663861, compound

Product 1

HCID 86663862HCID 86663862, compoundYield 53.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of (2RS,3SR)-3-(3,4-dichlorophenyl)oxirane-2-carboxylic acid (50.0 g) and 2-(benzylamino)ethanol (38.9 g) in THF (700 mL)-methanol (100 mL) was added 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (71.2 g), and the mixture was stirred at room temperature overnight. The reaction solution was concentrated, the residue was diluted with ethyl acetate, and the mixture was washed with saturated aqueous sodium hydrogen carbonate, water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (42.2 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washthe mixture was washed with saturated aqueous sodium hydrogen carbonate, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-fd19eeee03134b43a64c9b7478d67d8e
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…