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

Temperature

2.5 °C

Taurine (1 g; 8 mmol) was dissolved in 2N NaOH (4.3 mL) and, after cooling on ice/water bath, 4N NaOH (2.14 mL) and a solution of benzyloxycarbonyl chloride (3.27 mL; 8 mmol) in toluene (3 mL) were dropped at same time. After the additions, the mixture was left stirring at T=0-5° C. for 1 h. The reaction was quenched by adding diethyl ether. The mixture was debated and the phases were separated. The aqueous one was cooled to 0-5° C. and 37% HCl was added to pH=2. The acidic phase was extracted with ethyl acetate (3×10 mL) and the collected organic extracts were washed with water (2×15 mL) and brine (15 mL), dried over Na2SO4 and evaporated under vacuum to give 2-(N-benzyloxycarbonylamino)ethanesulfonic acid as crude product purified by trituration in diethyl ether to give the pure product as white solid (1.46 g; 5.64 mmol Yield=70.5%)

1. temperatureafter cooling on ice/water bath
2. waitAfter the additions, the mixture was left
3. customThe reaction was quenched
4. additionby adding diethyl ether
5. customthe phases were separated
6. temperatureThe aqueous one was cooled to 0-5° C.
7. addition37% HCl was added to pH=2
8. extractionThe acidic phase was extracted with ethyl acetate (3×10 mL)
9. washthe collected organic extracts were washed with water (2×15 mL) and brine (15 mL)
10. dry with materialdried over Na2SO4
11. customevaporated under vacuum

ORD record

ord-6a8d20b787fc435eaeaea62f4a13a8aa

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06881755B2