Water → HCID 87066192, compound

HRID 1518623Notes

Reaction equation

HRID 1518623 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[S:21]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([OH:24])(=[O:23])=[O:22].O>C1(C)C=CC=CC=1.C(O)C1C=CC=CC=1>[S:21]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)([OH:24])(=[O:23])=[O:22].[NH2:1][C:2]1[CH:3]=[C:4]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH2:29][C:28]2[CH:30]=[CH:31][CH:25]=[CH:26][CH:27]=2)=[O:18])[CH:5]=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 66597004HCID 66597004, compound

Product 1

HCID 87066192HCID 87066192, compoundYield 171.2%

Reagents, catalysts & solvents 2

HCID 244Benzyl AlcoholSolventHCID 1140TolueneSolvent

Procedure

To a suspension of 4-(3-Amino-4-phenylphenyl)butyric acid (21.6 g, 84.6 mmol) in toluene (300 mL), benzyl alcohol (50 mL) and tosylic acid hydrate (17.7 g, 93.0 mmol) were added, and the mixture was heated under reflux for 5 hours with water removed by a Dean-Stark trap. The reaction solution was concentrated under reduced pressure and a solid obtained was washed with a mixed solvent of hexane-ethyl acetate (4:1). The solid was collected by filtration and dried under reduced pressure to obtain benzyl 4-(3-amino-4-phenylphenyl)butyrate tosylate (41.2 g).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. customremoved by a Dean-Stark trap
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. customa solid obtained
  6. washwas washed with a mixed solvent of hexane-ethyl acetate (4:1)
  7. filtrationThe solid was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-2fa158d62ec74a38928f0596082c51e8
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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