Triphenylcarbinol → S-Tritylcysteamine

HRID 917565Notes

Reaction equation

HRID 917565 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:22][CH2:23][CH2:24][SH:25]>FC(F)(F)C(O)=O>[C:7]([S:25][CH2:24][CH2:23][NH2:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6457TriphenylcarbinolHCID 9082Cysteamine Hydrochloride

Product 1

HCID 262764S-TritylcysteamineYield 85%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triphenylmethanol (22.9 g, 88 mmol) was added to a solution of 2-aminoethanethiol hydrochloride in trifluroacetic acid (TFA, 40 mL). The resulting solution was stirred at room temperature for about 40 min. The TFA was then removed under reduced pressure and the residue was triturated with diethyl ether. The white precipitate that formed was filtered, partitioned with aqueous NaOH (40 mL, 1N), and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. The product was obtained as a white solid after solvent evaporation (23.8 g, yield 85%). ESI-MS(m/z): 320 (M+H+). 1H NMR δD (CDCl3): 7.21˜7.43 (m, 15H, phenyl), 2.58 (t, 2H, SCH2), 2.32 (t, 2H, CH2N).

Workup

  1. customThe TFA was then removed under reduced pressure
  2. customthe residue was triturated with diethyl ether
  3. customThe white precipitate that formed
  4. filtrationwas filtered
  5. custompartitioned with aqueous NaOH (40 mL, 1N)
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. customThe product was obtained as a white solid
  9. customafter solvent evaporation (23.8 g, yield 85%)

Sources & evidence

ORD record
ord-beb743dccb7d4e47aa71050bdc64c3f9
Source dataset
uspto-grants-2007_09
Patent number
US07273904B2

Reaction notes

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