Taurine → HCID 57345279, compound

HRID 1716163Notes

Reaction equation

HRID 1716163 reaction equation
[NH2:1][CH2:2][CH2:3][S:4]([OH:7])(=[O:6])=[O:5].[CH2:8]([O:15][C:16](Cl)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+:23]>[OH-].[Na+].O>[Na+:23].[CH2:8]([O:15][C:16]([NH:1][CH2:2][CH2:3][S:4]([O-:7])(=[O:6])=[O:5])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 1123TaurineHCID 10387Benzyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 57345279HCID 57345279, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Procedure

Taurine, 1 (about 40 g, 320 mmols), was dissolved in 4N sodium hydroxide solution (80 mL) and water (about 200 mL). To this solution was added benzyloxycarbonyl chloride, (about 48 mL, 330 mmols) dropwise, with vigorous stirring during a period of about 4 hours. The pH of the solution was maintained alkaline by the addition of 10% sodium bicarbonate solution (about 300 mL) and 4N sodium hydroxide solution (about 45 mL). The obtained reaction mixture was then washed with diethyl ether (about 1000 mL) and the aqueous layer was rotary evaporated to dryness, and further dried under high vacuum over phosphorous pentoxide overnight to yield about 12.7 g (14%) of 2. 1H-NMR (D2O): δ 7.50 (5H, s, Ar—H), 5.21 (2H, s, Ar—CH2), 3.62 (2H, t, CH2), 3.14 (2H, t, CH2).

Workup

  1. temperatureThe pH of the solution was maintained alkaline
  2. customThe obtained reaction mixture
  3. washwas then washed with diethyl ether (about 1000 mL)
  4. customthe aqueous layer was rotary evaporated to dryness
  5. dry with materialfurther dried under high vacuum over phosphorous pentoxide overnight

Sources & evidence

ORD record
ord-614e60974d214940be8f276eaf5fada3
Source dataset
uspto-grants-2010_09
Patent number
US07803399B2

Reaction notes

Loading…