Taurine → 2-{[(Benzyloxy)carbonyl]amino}ethane-1-sulfonic acid

HRID 897333Notes

Reaction equation

HRID 897333 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>O>[CH2:12]([O:11][C:9]([NH:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 1123TaurineHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformate

Product 1

HCID 154820532-{[(Benzyloxy)carbonyl]amino}ethane-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of taurine (12.5 g, 100 mmol), benzyl chloroformate (15.1 mL, 105 mmol) and sodium carbonate (10.6 g, 100 mmol) in water (250 mL) was stirred at room temperature for overnight. The product mixture was extracted with diethyl ether. The organic extract was concentrated under vacuum to provide 2-{[(benzyloxy)carbonyl]-amino}ethanesulfonic acid. Without further purification, the sulfonic acid was treated with thionyl chloride (15 mL, 206 mmol) with external ice-water bath cooling. The resultant mixture was stirred at room temperature for 1 hour, and poured into ice water. The mixture was extracted with diethyl ether. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide the title compound as white solid.

Workup

  1. extractionThe product mixture was extracted with diethyl ether
  2. extractionThe organic extract
  3. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-31b8dd967d5a4552aa228ab3706fe8a0
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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