Acetate → HCID 19063413, compound

HRID 1900154Notes

Reaction equation

HRID 1900154 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].Cl[CH2:6][O:7][C:8]([O:10][CH:11]([CH3:19])[CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])=[O:9]>C1COCC1>[C:1]([O:4][CH2:6][O:7][C:8]([O:10][CH:11]([CH3:19])[CH2:12][NH:13][C:14](=[O:18])[C:15]([CH3:17])=[CH2:16])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 175AcetateHCID 19063424HCID 19063424, compound

Product 1

HCID 19063413HCID 19063413, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution (30 ml) of TBA acetate (1.21 g, 4 mmol), prepared by freeze-drying an aqueous solution of equimolar TBA-OH and acetic acid, was added to a stirred solution of N-(2-chloromethoxycarbonyloxypropyl) methacrylamide (0.943 g, 4 mmol) from Example 16 above in THF (10 ml) at room temperature. Following stirring for 5 days the solvent was removed under reduced pressure and the residue was dissolved in chloroform (50 ml) and washed with water (5×10 ml). The organic phase was dried (MgSO4) and the solvent removed under reduced pressure. Flash chromatography (silicagel, hexane/ethyl acetate (3:4)) gave 0.486 g (47%) 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 (50 ml)
  4. washwashed with water (5×10 ml)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-759ad50f9d324028ac00062a45c717db
Source dataset
uspto-grants-1996_11
Patent number
US05574097

Reaction notes

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