Water → HCID 19001968, compound

HRID 2259978Notes

Reaction equation

HRID 2259978 reaction equation
[CH3:1][N:2]([C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]([CH2:32][C:33]([O:35]C(C)(C)C)=[O:34])[C:18](=[O:31])[CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>FC(F)(F)C(O)=O>[CH3:1][N:2]([C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]([CH2:32][C:33]([OH:35])=[O:34])[C:18](=[O:31])[CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30])=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 962WaterHCID 15670999HCID 15670999, compound

Product 1

HCID 19001968HCID 19001968, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-{N-[2-(N-Methylanilino)carbonylphenyl]-2-phthalimidoacetamideo}acetic acid may be prepared in the following manner: a solution of tert-butyl 2-{N-[2-(N-methylanilino)carbonylphenyl]-2-phthalimidoacetamido]acetate (7.9 g) in trifluoroacetic acid (30 cc) is stirred at a temperature in the region of 20° C. for 24 hours and then poured into water (50 cc). The aqueous phase is extracted with dichloromethane (3×250 cc). The organic phases are combined, washed with water (2×150 cc), dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa) at 60° C. The residue is treated with petroleum ether (100 cc) and the insoluble product is separated by filtration and dried under reduced pressure (15 kPa) at 30° C. 2-{N-[2-(N-Methylanilino)carbonylphenyl]-2-phthalimidoacetamido}acetic acid (6.8 g) is thereby obtained in the form of an amorphous solid, which is used without further treatment in the subsequent syntheses.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane (3×250 cc)
  2. washwashed with water (2×150 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 60° C
  6. additionThe residue is treated with petroleum ether (100 cc)
  7. customthe insoluble product is separated by filtration
  8. customdried under reduced pressure (15 kPa) at 30° C

Sources & evidence

ORD record
ord-fda65d7f7cfb4a9ea93daa9c697db5a8
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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