Acetate → HCID 19063417, compound

HRID 1900155Notes

Reaction equation

HRID 1900155 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].Cl[CH:6]([O:8][C:9]([O:11][CH:12]([CH3:20])[CH2:13][NH:14][C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])=[O:10])[CH3:7]>C1COCC1>[C:1]([O:4][CH:6]([O:8][C:9]([O:11][CH:12]([CH3:20])[CH2:13][NH:14][C:15](=[O:19])[C:16]([CH3:18])=[CH2:17])=[O:10])[CH3:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 175AcetateHCID 19063419HCID 19063419, compound

Product 1

HCID 19063417HCID 19063417, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution (100 ml) of TBA acetate (6.93 g, 23 mmol), prepared by freeze-drying an aqueous solution of equimolar TBA-OH and acetic acid, was added to a stirred solution of N-[2-(1-chloroethoxycarbonyloxy)propyl]methacrylamide (4.736 g, 19 mmol) in THF (100 ml) at room temperature. Following stirring for 4 days the solvent was removed under reduced pressure and the residue was dissolved in chloroform (100 ml) and washed with water (5×20 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography (silicagel, hexane/ethyl acetate (3:4)) gave 1.29 g (25%) of the title product.

Workup

  1. dry with materialby freeze-drying an aqueous solution of equimolar TBA-OH and acetic acid
  2. customwas removed under reduced pressure
  3. dissolutionthe residue was dissolved in chloroform (100 ml)
  4. washwashed with water (5×20 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d683182a5e4a4b04bf349bbc548490a2
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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