Réaction #1684

Équation de réaction

Cbz-D-hPro-OH

2,4,5-trichlorophenol

Pro-OH

triethylamine

1,3-dicyclohexylcarbodiimide

→

Cbz-D-hPro-Pro-OH

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONAdded to the solution
2. 2
   FiltrationThe precipitate was filtered
3. 3
   Concentrationthe filtrate concentrated in vacuo to an oil
4. 4
   workup.DISSOLUTIONThe oil was dissolved in pyridine (100 mL)
5. 5
   workup.STIRRINGThe reaction was stirred at room temperature (24 hours)
6. 6
   AutreThe reaction solvent was removed in vacuo to an oil
7. 7
   workup.DISSOLUTIONThe residue was dissolved in water (100 mL)
8. 8
   workup.ADDITIONdiethyl ether (50 mL) was added
9. 9
   ExtractionThe aqueous layer extracted twice with diethyl ether
10. 10
    AutreThe aqueous layer separated
11. 11
    workup.ADDITIONwas added
12. 12
    AutreThe organic layer was separated
13. 13
    Séchagedried (MgSO4)
14. 14
    Autrethe filtrate evaporated in vacuo to an amorphous solid (11.4 g, 88%)

Mode opératoire

Cbz-D-hPro-OH (9.5 g, 36 mmol) was dissolved in ethyl acetate (100 mL) and the solution cooled to 0° C. Added to the solution was 2,4,5-trichlorophenol (7.1 g, 36 mmol) and 1,3-dicyclohexylcarbodiimide (7.4 g, 36 mmol). The reaction was stirred for 1 hour at 0° C. and 1 hour at room temperature. The precipitate was filtered and the filtrate concentrated in vacuo to an oil. The oil was dissolved in pyridine (100 mL), Pro-OH (4.2 g, 36 mmol), and triethylamine (5.0 mL, 36 mmol) were added. The reaction was stirred at room temperature (24 hours). The reaction solvent was removed in vacuo to an oil. The residue was dissolved in water (100 mL), diethyl ether (50 mL) was added and the pH adjusted to 9.5 with 2N sodium hydroxide. The aqueous layer extracted twice with diethyl ether. The aqueous layer separated, the pH adjusted to 2.8 with 3N hydrochloric acid and ethyl acetate (150 mL) was added. The organic layer was separated, dried (MgSO4), and the filtrate evaporated in vacuo to an amorphous solid (11.4 g, 88%).

Source