Cysteamine → S-Tritylcysteamine

HRID 2201281Notes

Reaction equation

HRID 2201281 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>C(O)(C(F)(F)F)=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-Tritylcysteamine

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Cysteamine (commercial) (900 mg, 11.67 mmol) was added to a stirred solution of triphenylmethanol (commercial) (3.037 g, 11.67 mmol) in TFA (10 ml) and the mixture stirred at RT for 3 hours. The mixture was then concentrated under reduced pressure and the residue partitioned between DCM (20 mL) and water (20 mL). The mixture was basified by the slow addition of solid K2CO3. The aqueous phase was extracted with DCM (2×20 mL), the combined organic phases passed through a hydrophobic frit and the solvent evaporated under reduced pressure. The material was used without further purification.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customthe residue partitioned between DCM (20 mL) and water (20 mL)
  3. additionThe mixture was basified by the slow addition of solid K2CO3
  4. extractionThe aqueous phase was extracted with DCM (2×20 mL)
  5. customthe solvent evaporated under reduced pressure
  6. customThe material was used without further purification

Sources & evidence

ORD record
ord-9cb17ab01d0c4f6aa103d850895b45fc
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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