Trifluoroacetic acid → S-Tritylcysteamine

HRID 909467Notes

Reaction equation

HRID 909467 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].Cl.FC(F)(F)C(O)=O.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>ClCCl>[C:19]([S:4][CH2:3][CH2:2][NH2:1])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6456Trityl chlorideHCID 9082Cysteamine HydrochlorideHCID 14798Sodium Hydroxide

Product 1

HCID 262764S-TritylcysteamineYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrochloric acid 2-aminoethanethiol (5.16 g, 45.4 mmol) was dissolved in dichloromethane (80 mL), and trifluoroacetic acid (7.0 mL, 90.8 mmol) and triphenylmethyl chloride (13.29 g, 47.7 mmol) were added, followed by stirring at room temperature for 1 hour. A 1N aqueous sodium hydroxide solution (150 mL) was added, and extraction was carried out with dichloromethane (500 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, methanol (100 mL) was added to the resulting residue, and the deposited by-product was removed by filtration. 1N hydrochloric acid (300 mL) was added to make the solution acidic, and the deposit was filtered off. After the by-product was washed with dichloromethane (50 mL) to remove it, the solution was made alkaline with a 1N aqueous sodium hydroxide solution, and extraction was carried out with dichloromethane (600 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to afford the desired product (8.77 g, yield 60%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure, methanol (100 mL)
  5. additionwas added to the resulting residue
  6. customthe deposited by-product was removed by filtration
  7. addition1N hydrochloric acid (300 mL) was added
  8. filtrationthe deposit was filtered off
  9. washAfter the by-product was washed with dichloromethane (50 mL)
  10. customto remove it
  11. extractionwith a 1N aqueous sodium hydroxide solution, and extraction
  12. washThe organic layer was washed with saturated brine
  13. dry with materialsubsequently dried over anhydrous magnesium sulfate
  14. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c25d2cc6e48c462b966c9519c24a68c7
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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