Water → HCID 22917836, compound

HRID 2259963Notes

Reaction equation

HRID 2259963 reaction equation
[K].[C:2]1(=[O:12])[NH:6][C:5](=[O:7])[C:4]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:3]12.Cl[CH2:14][C:15]([N:17]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=[O:16].O>CN(C)C=O>[CH3:25][O:24][C:20]1[CH:19]=[C:18]([N:17]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:15](=[O:16])[CH2:14][N:6]2[C:2](=[O:12])[C:3]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:4]3[C:5]2=[O:7])[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 19002001HCID 19002001, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 22917836HCID 22917836, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 2-[N-(3-methoxyphenyl)-2-phthalimidoacetamido] acetate may be prepared in the following manner: phthalimide potassium salt (7.5 g) is added to a solution of tert-butyl 2-[2-chloro-N-(3-methoxyphenyl)acetamido]acetate (6.3 g) in dimethylformamide (100 cc). The mixture is stirred at a temperature in the region of 100° C. for 5 hours and then poured into water (1000 cc). The insoluble product is separated by filtration, washed with water (3×60 cc) and dried in the air. After recrystallisation in diisopropyl ether, tert-butyl 2-[N-(3-methoxyphenyl)-2-phthalimidoacetamido]acetate (6.7 g), m p 138° C. is obtained.

Workup

  1. customThe insoluble product is separated by filtration
  2. washwashed with water (3×60 cc)
  3. customdried in the air
  4. customAfter recrystallisation in diisopropyl ether

Sources & evidence

ORD record
ord-e6ba3ea41575453ebb23b63cd803448f
Source dataset
uspto-grants-1995_12
Patent number
US05475106

Reaction notes

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