Anisole → HCID 19422436, compound

HRID 744876Notes

Reaction equation

HRID 744876 reaction equation
COC1C=CC(COC([N:11]2[CH2:16][CH2:15][N:14]([C:17](=[O:33])[CH2:18][NH:19][C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])[CH2:13][CH2:12]2)=O)=CC=1.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[N+:30]([C:27]1[CH:26]=[CH:25][C:24]([CH2:23][O:22][C:20]([NH:19][CH2:18][C:17]([N:14]2[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)=[O:33])=[O:21])=[CH:29][CH:28]=1)([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 19422423HCID 19422423, compound

Product 1

HCID 19422436HCID 19422436, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 3.74 g of 1-(p-methoxybenzyloxycarbonyl)-4-(2-(p-nitrobenzyloxycarbonyl)aminoacetyl)piperazine were added 4.17 ml of anisole and, with cooling on an ice bath, 20 ml of trifluoroacetic acid, followed by 1 hour of reaction at room temperature. After removing trifluoroacetic acid by evaporation under a reduced pressure, the residue was adjusted to basic with a sodium hydroxide aqueous solution and extracted with chloroform, and an organic layer was washed with water and dried over sodium sulfate, followed by removal of the solvent under a reduced pressure and subsequent addition of n-hexane to a residue to collect a solid material by filtration, thereby obtaining 2.45 g of 1-(2-(p-nitrobenzyloxycarbonyl)aminoacetyl)piperazine.

Workup

  1. temperaturewith cooling on an ice bath
  2. customAfter removing trifluoroacetic acid
  3. customby evaporation under a reduced pressure
  4. extractionextracted with chloroform
  5. washan organic layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customfollowed by removal of the solvent under a reduced pressure and subsequent addition of n-hexane to a residue
  8. customto collect a solid material
  9. filtrationby filtration

Sources & evidence

ORD record
ord-3be2f55d706545cfaafe345b2f2f729c
Source dataset
uspto-grants-1996_09
Patent number
US05559224

Reaction notes

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