Water → HCID 13557219, compound

HRID 1583481Notes

Reaction equation

HRID 1583481 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8]C(OC(C)(C)C)=O)[CH:5]=[CH:4][C:3]=1[CH2:16][N:17]1[C:21](=[O:22])[C:20]([CH3:24])([CH3:23])[CH2:19][O:18]1.FC(F)(F)C(O)=O.O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:16][N:17]2[C:21](=[O:22])[C:20]([CH3:23])([CH3:24])[CH2:19][O:18]2)=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 13557261HCID 13557261, compound

Product 1

HCID 13557219HCID 13557219, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2.0 grams (0.006 mole) of 2-[2-chloro-4-(1,1-dimethylethoxycarbonylamino)phenyl]methyl-4,4-dimethyl-3-isoxazolidinone in 10 ml of methylene chloride was added dropwise a solution of 10 ml of trifluoroacetic acid in 10 ml of methylene chloride. Upon completion of addition the reaction mixture stirred at ambient temperature for 3.5 hours. The reaction mixture was slurried with 50 ml of water and neutralized with a saturated aqueous solution of potassium carbonate. A solid precipitate was collected by filtration to give 1.3 grams of 2-(4-amino-2-chlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone; m.p. 106°-108° C.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. filtrationA solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-676246f099f04dd59fe27d9c3082f9a0
Source dataset
uspto-grants-1985_11
Patent number
US04552585

Reaction notes

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