Water → HCID 13299003, compound

HRID 544498Notes

Reaction equation

HRID 544498 reaction equation
[CH3:1][C@H:2]([CH2:6][SH:7])[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].O.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][C:17]=1[S:25](=[O:28])(=[O:27])[NH2:26]>CCOCC>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([S:7][CH2:6][C@@H:2]([CH3:1])[C:3]([OH:5])=[O:4])=[O:21])=[CH:18][C:17]=1[S:25](=[O:27])(=[O:28])[NH2:26]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 10154042HCID 10154042, compound

Product 1

HCID 13299003HCID 13299003, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3 g of 2(S)-methyl-3-mercaptopropionic acid is added to a mixture of 3.5 g of potassium carbonate, 60 ml of water and 30 ml of ether with stirring atroom temperature under a nitrogen atmosphere whereupon 6.3 g of 4-chloro-3-sulfamoylbenzoyl chloride is added, and the resulting mixture is stirred at room temperature for 5.5 hours. The aqueous layer is then collected and made acidic with dilute hydrochloric acid, and the separatedoil is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Isopropyl ether is added to the residual oil. The crystals thus obtained are recrystallized from a mixture of ethyl acetate and hexane to give 3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionic acid as white crystalline powder, melting at 152°-153° C. (sinteringat 145° C.).

Workup

  1. additionis added
  2. customThe aqueous layer is then collected
  3. extractionthe separatedoil is extracted with ethyl acetate
  4. washThe extract is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionIsopropyl ether is added to the residual oil
  8. customThe crystals thus obtained
  9. customare recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-bc86cc3a31a544a198700de8dc3c0622
Source dataset
uspto-grants-1984_05
Patent number
US04450275

Reaction notes

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