p-Toluenesulfonic acid → Bis(3-phthalimidopropyl)acetic acid

HRID 1654591Notes

Reaction equation

HRID 1654591 reaction equation
[C:1]1(=[O:43])[N:5]([CH2:6][CH2:7][CH2:8][C:9]([CH2:24][CH2:25][CH2:26][N:27]2[C:31](=[O:32])[C:30]3=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]3[C:28]2=[O:37])(C(OC(C)(C)C)=O)[C:10]([O:12]C(C)(C)C)=[O:11])[C:4](=[O:38])[C:3]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:2]12.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:28]1(=[O:37])[N:27]([CH2:26][CH2:25][CH2:24][CH:9]([CH2:8][CH2:7][CH2:6][N:5]2[C:4](=[O:38])[C:3]3=[CH:39][CH:40]=[CH:41][CH:42]=[C:2]3[C:1]2=[O:43])[C:10]([OH:12])=[O:11])[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]12

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20077931Di-tert-butyl bis(3-phthalimidopropyl)malonate

Product 1

HCID 20077933Bis(3-phthalimidopropyl)acetic acidYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of di-tert-butyl Bis(3-phthalimidopropyl)malonate (Step A) (6 g, 10.16 mmol), a catalytic amount of PTSA in 60 mL of toluene is heated to reflux for 4 hours. The reaction is cooled and a solid is filtered and dried. The solid is heated neat (under a nitrogen atmosphere) for 2 hours. From this procedure 3.81 g of Bis(3-phthalimidopropyl)acetic acid is isolated.

Workup

  1. temperatureto reflux for 4 hours
  2. temperatureThe reaction is cooled
  3. filtrationa solid is filtered
  4. customdried
  5. temperatureThe solid is heated neat (under a nitrogen atmosphere) for 2 hours

Sources & evidence

ORD record
ord-619393d27ee5472895d80aea7ebbdf05
Source dataset
uspto-grants-1995_04
Patent number
US05407916

Reaction notes

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