3-Aminobenzenesulfonic acid → (2S)-2-amino-3-{[(3-sulfophenyl)carbamothioyl]amino}propanoic acid

HRID 1746831Notes

Reaction equation

HRID 1746831 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([OH:11])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].[C:17](Cl)(Cl)=[S:18].Cl.[NH2:22][CH2:23][C@H:24]([NH:32]C(OC(C)(C)C)=O)[C:25]([O:27]C(C)(C)C)=[O:26]>C1COCC1.O>[NH2:32][C@@H:24]([CH2:23][NH:22][C:17](=[S:18])[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([S:8]([OH:11])(=[O:9])=[O:10])[CH:3]=1)[C:25]([OH:27])=[O:26]

Participants

7

Reactant 4

HCID 84743-Aminobenzenesulfonic acidHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 86679032(S)-tert-Butyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate hydrochloride

Product 1

HCID 86679035(2S)-2-amino-3-{[(3-sulfophenyl)carbamothioyl]amino}propanoic acidYield 5.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

35 mg (0.2 mmol) of 3-aminobenzenesulfonic acid and 57 mg (0.68 mmol) of sodium hydrogen carbonate were added to a mixed solvent of 2.0 ml of water and 0.5 ml of THF, and stirred at room temperature for 15 minutes. 20 μl (0.26 mmol) of thiophosgene was added and stirred at room temperature for another 40 minutes. Subsequently, 60 mg (0.2 mmol) of tert-butyl (2S)-3-amino-2-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride was added and stirred overnight. Following extraction with ethyl acetate, the solvent was distilled away, and 4.0 ml of trifluoroacetic acid was added to the residue, and the resultant was stirred at room temperature for 5 hours. After distilling the solvent away, purification step A was used to obtain 3.5 mg of the title compound.

Workup

  1. stirringstirred at room temperature for another 40 minutes
  2. stirringstirred overnight
  3. extractionextraction with ethyl acetate
  4. distillationthe solvent was distilled away
  5. addition4.0 ml of trifluoroacetic acid was added to the residue
  6. stirringthe resultant was stirred at room temperature for 5 hours
  7. distillationAfter distilling the solvent away
  8. custompurification step A

Sources & evidence

ORD record
ord-bb6cd2f7438946de8351c5756f7cb2ed
Source dataset
uspto-grants-2015_10
Patent number
US09150505B2

Reaction notes

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