Hydrochloric Acid → HCID 12893584, compound

HRID 544493Notes

Reaction equation

HRID 544493 reaction equation
[SH:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]1[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][S:8][CH2:7]1)=[O:5].C(=O)([O-])O.[Na+].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][C:22]=1[S:30](=[O:33])(=[O:32])[NH2:31].Cl>O>[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([S:1][CH2:2][C@@H:3]([CH3:14])[C:4]([N:6]2[C@H:10]([C:11]([OH:13])=[O:12])[CH2:9][S:8][CH2:7]2)=[O:5])=[O:26])=[CH:23][C:22]=1[S:30](=[O:32])(=[O:33])[NH2:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 171857YS 980HCID 516892Sodium BicarbonateHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chloride

Product 1

HCID 12893584HCID 12893584, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.5 g of 3-[3-mercapto-2(S)-methylpropionyl]-4(R)-thiazolidinecarboxylic acid and 2 g of sodium hydrogen carbonate are added to 150 ml of water whereupon 2.5 g of 4-chloro-3-sulfamoylbenzoyl chloride is added slowly under ice-cooling and stirring, and the resulting mixture is stirred at room temperature for 3 hours. The reaction mixture is then made acidic with dilute hydrochloric acid under ice-cooling, and the non-crystalline solid is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The non-crystalline solid thus obtained is purified by column chromatography on silica gel with ethyl acetate-hexane (4:1) eluants. Thusis obtained 3-[3-(4-chloro-3-sulfamoylbenzoylthio)-2(S)-methylpropionyl]-4(R)-thiazolidinecarboxylic acid as white non-crystalline powder, [α]D25 -118.8 (methanol). The dicylohexylamine salt of this product has a meltingof 173°-176° C.

Workup

  1. additionis added slowly under ice-
  2. temperaturecooling
  3. stirringthe resulting mixture is stirred at room temperature for 3 hours
  4. extractionthe non-crystalline solid is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe non-crystalline solid thus obtained
  9. customis purified by column chromatography on silica gel with ethyl acetate-hexane (4:1) eluants

Sources & evidence

ORD record
ord-ac31b30fb5ac4a628a46f784917a05fc
Source dataset
uspto-grants-1984_05
Patent number
US04450275

Reaction notes

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