Glycine → HCID 131726843, compound

HRID 902583Notes

Reaction equation

HRID 902583 reaction equation
[CH2:1]([NH2:5])[C:2]([OH:4])=[O:3].C([O-])(O)=O.[Na+].[CH2:11]([C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19]([NH:29][CH3:30])=[C:20]2[S:25](Cl)(=[O:27])=[O:26])[CH2:12][CH2:13][CH3:14]>O.CC(C)=O>[CH2:11]([C:15]1[CH:24]=[CH:23][CH:22]=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19]([NH:29][CH3:30])=[C:20]2[S:25]([NH:5][CH2:1][C:2]([OH:4])=[O:3])(=[O:27])=[O:26])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 3

HCID 750GlycineHCID 516892Sodium BicarbonateHCID 86606595HCID 86606595, compound

Product 1

HCID 131726843HCID 131726843, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Two mmoles of L-glycine and 3 mmoles of NaHCO3 were dissolved in 5 ml of water. A solution containing 1 mmol of 3 in acetone was slowly added. More acetone was added until the solution was clear. The mixture was stirred overnight at room temperature, and protected from light. Acetone was removed by flash evaporation and the remaining water solution was acidified to pH=4.5 to 5 by adding 2M citric acid. Then, NaCl was added until saturation and the solution was extracted with three portions of ethyl acetate (20 ml each). The extracts were combined, dried over MgSO4 and solution filtered Solvent was removed and residue purified by liquid chromatography on silica gel. A gradient of 0 to 5% methanol in dichloromethane was used as eluent. Fractions containing desired products were combined and solvents removed. The residue was triturated in 1:1 ether: petroleum ether. Precipitate was filtered out and dried in vacuum overnight thus affording 5-Butylmethylamino-naphtalene-1-sulfonyl-glycine (NST703).

Workup

  1. additionwas slowly added
  2. customAcetone was removed by flash evaporation
  3. additionby adding 2M citric acid
  4. additionThen, NaCl was added until saturation
  5. extractionthe solution was extracted with three portions of ethyl acetate (20 ml each)
  6. dry with materialdried over MgSO4 and solution
  7. filtrationfiltered Solvent
  8. customwas removed
  9. customresidue purified by liquid chromatography on silica gel
  10. additionFractions containing desired products
  11. customsolvents removed
  12. customThe residue was triturated in 1:1 ether
  13. filtrationPrecipitate was filtered out
  14. dry with materialdried in vacuum overnight thus affording 5-Butylmethylamino-naphtalene-1-sulfonyl-glycine (NST703)

Sources & evidence

ORD record
ord-92db2c75522d44579e4c647e54fc90f7
Source dataset
uspto-grants-2008_04
Patent number
US07365223B2

Reaction notes

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