5-Aminovaleric acid → 4-Methylbenzene-1-sulfonic acid--benzyl 5-aminopentanoate (1/1)

HRID 436956Notes

Reaction equation

HRID 436956 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].O.[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16]([OH:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.C1C=CC=CC=1.[CH2:27](O)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:10]1([CH3:20])[CH:11]=[CH:12][C:13]([S:16]([OH:19])(=[O:17])=[O:18])=[CH:14][CH:15]=1.[CH2:27]([O:7][C:6](=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2][NH2:1])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 241BenzeneHCID 244Benzyl AlcoholHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 567770174-Methylbenzene-1-sulfonic acid--benzyl 5-aminopentanoate (1/1)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

11.7 Parts 5-aminopentanoic acid and 22.8 parts p-toluenesulfonic acid monohydrate is suspended in 180 parts benzene and 32.4 parts benzyl alcohol is added. A continuous water separator is attached to the flask and the mixture stirred at vigorous reflux temperature for 16 hours. After cooling to room temperature, the solvent is removed under reduced pressure and the residual oil shaken with n-hexane. The supernatant is discarded and the gummy product rubbed with ethyl ether causing crystallization to take place. The solid is separated, by filtration and washed with ethyl ether to afford the desired 5-aminopentanoic acid benzyl ester p-toluenesulfonate.

Workup

  1. additionis added
  2. customthe solvent is removed under reduced pressure
  3. stirringthe residual oil shaken with n-hexane
  4. customthe gummy product rubbed with ethyl ether causing crystallization
  5. customThe solid is separated, by filtration
  6. washwashed with ethyl ether

Sources & evidence

ORD record
ord-52425f4b829a411e87bb03d554374250
Source dataset
uspto-grants-1977_06
Patent number
US04028319

Reaction notes

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