Cysteamine → S-Tritylcysteamine

HRID 2221121Notes

Reaction equation

HRID 2221121 reaction equation
[NH2:1][CH2:2][CH2:3][SH:4].[C:5]1([C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>FC(F)(F)C(O)=O>[C:11]([S:4][CH2:3][CH2:2][NH2:1])([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6058CysteamineHCID 6457Triphenylcarbinol

Product 1

HCID 262764S-TritylcysteamineYield 58%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a stirred solution of cysteamine (Fluka, 3.85 g, 50.0 mmol) in trifluoroacetic acid (TFA) (50 ml) was added triphenylmethanol (13.0 g, 50.0 mmol). The mixture was stirred at room temperature for 30 min and concentrated. To the residue was added ether (250 ml). Precipitated material was filtered off and washed with ether. The TFA-salt was partitioned between 1 M aqueous KOH solution (150 ml) and ether (150 ml). The phases were separated and the ether phase was dried (MgSO4). The solution was filtered and concentrated and the product was crystallised from ether/n-hexane, giving 9.20 g (58%) of white solid.

Workup

  1. concentrationconcentrated
  2. additionTo the residue was added ether (250 ml)
  3. filtrationPrecipitated material was filtered off
  4. washwashed with ether
  5. customThe TFA-salt was partitioned between 1 M aqueous KOH solution (150 ml) and ether (150 ml)
  6. customThe phases were separated
  7. dry with materialthe ether phase was dried (MgSO4)
  8. filtrationThe solution was filtered
  9. concentrationconcentrated
  10. customthe product was crystallised from ether/n-hexane

Sources & evidence

ORD record
ord-fd802aa4b8fe452ab2e8364bc9defcbd
Source dataset
uspto-grants-2008_05
Patent number
US07368474B2

Reaction notes

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