Gamma-Aminobutyric Acid → (4-Morpholinophenylsulphonylamino)butyric acid

HRID 373715Notes

Reaction equation

HRID 373715 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[NH2:17]CCCC(O)=O.[OH-].[Na+].O1[CH2:30][CH2:29]CC1.[C:31]([OH:34])(=[O:33])[CH3:32]>O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:17][CH:32]([CH2:29][CH3:30])[C:31]([OH:34])=[O:33])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 119Gamma-Aminobutyric AcidHCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 149512114-(Morpholin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 19811002(4-Morpholinophenylsulphonylamino)butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g of 4-morpholinobenzenesulphonyl chloride is added to a solution comprising 3.94 g of 4-amino butyric acid and 4.6 g of sodium hydroxide in 80 cm3 of water, then 70 cm3 of tetrahydrofuran is added so as to obtain a solution. The temperature increases from 20° to 27° C. The solution is allowed to return to ambient temperature and maintained under agitation for 24 hours, after which it is acidified with acetic acid, and the solvent is evaporated under reduced pressure. The residue is taken up with 50 cm3 of distilled water; the precipitate is filtered off, washed with water, dried and 7.6 g of expected product is obtained, m.p.=163°-165° C., which is recrystallized from ethyl acetate.

Workup

  1. customto obtain a solution
  2. temperatureThe temperature increases from 20° to 27° C
  3. customto return to ambient temperature
  4. temperaturemaintained under agitation for 24 hours
  5. customthe solvent is evaporated under reduced pressure
  6. filtrationthe precipitate is filtered off
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-c7d09ef79f4c437b980d8e7191d57d9d
Source dataset
uspto-grants-1992_11
Patent number
US05164514

Reaction notes

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