Sodium Sulfate → HCID 54532941, compound

HRID 1003653Notes

Reaction equation

HRID 1003653 reaction equation
S([O-])([O-])(=O)=O.[Na+].[Na+].[SH:8][CH2:9][C@@H:10]([CH3:28])[C:11]([NH:13][C@@H:14]([CH2:18][S:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=1)[C:15]([OH:17])=[O:16])=[O:12].O.[C:30]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[SH:8][CH2:9][C@@H:10]([CH3:28])[C:11]([NH:13][C@@H:14]([CH2:18][S:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=1)[C:15]([O:17][CH3:30])=[O:16])=[O:12]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 521998p-Toluenesulfonic acid monohydrateHCID 44581554HCID 44581554, compound

Product 1

HCID 54532941HCID 54532941, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Anhydrous sodium sulfate (3 g) is added to a solution of (2R)-2-[(2S)-3-mercapto-2-methylpropionylamino]-3-(4-methylbenzylthio)propionic acid (compound No. 1-1, 300 mg) and p-toluenesulfonic acid monohydrate (240 mg) in methanol (10 ml), and the mixture is refluxed for three hours and 30 minutes. Sodium sulfate is filtered out, and the filtrate is concentrated under reduced pressure. A 5% aqueous sodium hydrogencarbonate solution is added to the obtained residue, and the whole is extracted with ethyl acetate. The organic layer is washed with a 5% aqueous sodium hydrogencarbonate solution, a 5% aqueous citric acid solution and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the titled compound. The following compound is obtained by a method similar to Example 5.

Workup

  1. filtrationSodium sulfate is filtered out
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. additionA 5% aqueous sodium hydrogencarbonate solution is added to the obtained residue
  4. extractionthe whole is extracted with ethyl acetate
  5. washThe organic layer is washed with a 5% aqueous sodium hydrogencarbonate solution
  6. dry with materiala 5% aqueous citric acid solution and a saturated sodium chloride solution successively, dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2fe921ca47b64f4fa270e3e0a00232a8
Source dataset
uspto-grants-2000_04
Patent number
US06046235

Reaction notes

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