Reaction #985290

Reaction equation

12

Ferrocene-2-carboxylic acid [2-(pyridin-2-yldisulfanyl)-ethyl]-amide

DTT

Et3N

→

13

Yield 57.0%

Ferrocene-2-carboxylic acid (2-mercapto-ethyl)-amide

Yield 57.0%

Solvents

MeOH

Conditions

Workup

1. 1
   Otherfollowed by evaporation of the solvent
2. 2
   workup.DISSOLUTIONThe residue was dissolved in 15 mL of EtOAc
3. 3
   Washrinsed with H20 (8×15 mL)
4. 4
   Otherto remove excess DTT
5. 5
   DryingAfter drying over MgSO4
6. 6
   Concentrationconcentrating
7. 7
   Otherthe residue was purified by flash chromatography (hexanes/EtOAc, 1:1

Procedure

To a solution of 12 (113 mg, 0.28 mmol) dissolved in 6 mL of MeOH was added DTT (438 mg, 2.8 mmol) and Et3N (79 mL, 0.57 mmol). The solution was stirred at room temperature for 18 h, followed by evaporation of the solvent. The residue was dissolved in 15 mL of EtOAc and rinsed with H20 (8×15 mL) to remove excess DTT. After drying over MgSO4 and concentrating, the residue was purified by flash chromatography (hexanes/EtOAc, 1:1, v/v) to afford 46 mg (57%) of 13. 1H NMR 400 MHz (CDCl3) d 6.16 (br s, 1H), 4.66 (t, J=1.8 Hz, 2H), 4.33 (t, J=1.8 Hz, 2H), 4.19 (s, 5H), 3.53 (q, J=6.4 Hz, 2H), 2.75 (m, 2H).

Source