p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1447946Notes

Reaction equation

HRID 1447946 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[CH:10]([CH:28]([CH3:30])[CH3:29])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]=1)=[O:12].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(O)C>[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][N:2]1[CH:10]([CH:28]([CH3:30])[CH3:29])[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]=1)=[O:12]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20382862HCID 20382862, compound

Product 2

HCID 6101p-Toluenesulfonic acidHCID 20382862HCID 20382862, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To m-phenoxybenzyl 2-(2-isoindolinyl)-3-methylbutanoate (492 mg, 1.23 mmol) is added a solution of para-toluenesulfonic acid monohydrate (249 mg, 1.31 mmol) in 4 ml of 95% ethanol. The reaction mixture is allowed to stand for 2 hours at RT under nitrogen. The ethanol is removed under vacuum and the residue recrystallized from 30% hexane/benzene to yield the para-toluenesulfonic acid salt of m-phenoxybenzyl 2-(2-isoindolinyl)-3-methylbutanoate, m.p. 139°-140.3°.

Workup

  1. customThe ethanol is removed under vacuum
  2. customthe residue recrystallized from 30% hexane/benzene

Sources & evidence

ORD record
ord-a93ff0220ac14422a21f95420a258c7a
Source dataset
uspto-grants-1979_12
Patent number
US04178293

Reaction notes

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