Acetyl chloride → HCID 178437074, compound

HRID 399947Notes

Reaction equation

HRID 399947 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:30])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:25][CH:24]([CH2:26][CH3:27])[O:23][CH:22]([OH:28])[CH2:21]3)[C:11]=2[Cl:29])[CH:5]=[N:4]1)[CH3:2].[C:31](Cl)(=O)C>CO.ClCCl>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:30])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([N:20]3[CH2:25][CH:24]([CH2:26][CH3:27])[O:23][CH:22]([O:28][CH3:31])[CH2:21]3)[C:11]=2[Cl:29])[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178437075HCID 178437075, compound

Product 1

HCID 178437074HCID 178437074, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.08 g (2.35 mmol) of 1-ethyl-4-(2-chloro-3-(2-hydroxy-6-ethylmorpholin-4-yl)-4-methylsulfonylbenzoyl)-5-hydroxypyrazole in 5 mL of methanol was added with stirring to a solution of 20 mL of methanol pre-treated with 2 mL of acetyl chloride. After 1 hour, the mixture was diluted with dichloromethane and the resulting solution was washed with water and concentrated by evaporation under reduced pressure. The two component mixture residue obtained was separated and purified by preparative reverse-phase HPLC eluting with 1:1 acetonitrile/water containing 0.1 percent phosphoric acid. The fractions containing each of the two products were combined separately, concentrated by evaporation under reduced pressure and extracted with dichloromethane. The dichloromethane solutions were dried over sodium sulfate and concentrated by evaporation under reduced pressure to obtain the title compound as cis and trans isomers, both as syrups. There was 294 mg (27 percent of theory) of the more polar cis compound and 548 mg (49 percent of theory) of the less polar trans compound. These syrups were separately crystallized from ethanol to obtain the cis and trans isomers of the title compound as brown and off-white crystals, respectively.

Workup

  1. washthe resulting solution was washed with water
  2. concentrationconcentrated by evaporation under reduced pressure
  3. customThe two component mixture residue obtained
  4. customwas separated
  5. custompurified by preparative reverse-phase HPLC
  6. washeluting with 1:1 acetonitrile/water containing 0.1 percent phosphoric acid
  7. additionThe fractions containing each of the two products
  8. concentrationconcentrated by evaporation under reduced pressure
  9. extractionextracted with dichloromethane
  10. dry with materialThe dichloromethane solutions were dried over sodium sulfate
  11. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-3585dda3d2e84eebb1543e7bb23309ee
Source dataset
uspto-grants-1998_10
Patent number
US05824802

Reaction notes

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