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

HRID 981247Notes

Reaction equation

HRID 981247 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 obtian 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. temperatureThe temperature increases from 20° to 27° C
  2. customto return to ambient temperature
  3. temperaturemaintained under agitation for 24 hours
  4. customthe solvent is evaporated under reduced pressure
  5. filtrationthe precipitate is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-2fe5298a2ede4bcfb741c0d3fbc7a8f0
Source dataset
uspto-grants-1991_02
Patent number
US04990531

Reaction notes

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