Gamma-Aminobutyric Acid → HCID 54193138, compound

HRID 355137Notes

Reaction equation

HRID 355137 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([CH3:21])[CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27]>O.CC(C)=O.[OH-].[Na+]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][C@H:18]([CH3:20])[CH2:17][C@H:16]([CH3:21])[CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5]

Participants

6

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 54288570HCID 54288570, compound

Product 1

HCID 54193138HCID 54193138, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Chloro-5-(cis-3,5-dimethylpiperidinosulfonyl)benzoyl chloride (1.75 g.) is added to a solution of 4-aminobutyric acid (0.54 g.) in water (30 ml.), acetone (30 ml.) and 1 N sodium hydroxide (10 ml.). After stirring at room temperature for a half hour, the acetone is removed by evaporation, and the aqueous solution is acidified with concentrated hydrochloric acid. The precipitate is dissolved in 50 ml. of hot acetone-methanol (1:1) and concentrated to half volume. Hexane is added to crystallize the product, m.p. 193-°195° C.

Workup

  1. customthe acetone is removed by evaporation
  2. dissolutionThe precipitate is dissolved in 50 ml
  3. concentrationof hot acetone-methanol (1:1) and concentrated to half volume
  4. additionHexane is added
  5. customto crystallize the product
  6. customm.p. 193-°195° C.

Sources & evidence

ORD record
ord-deb877331d81405ea7ac38e62d8cd2c2
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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