Réaction #2254187

Équation de réaction

DIPEA

N-(tert-butoxycarbonyl)glycine

PYBOP

2,2,2-trifluorethylamine

→

[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Autrethe reaction is quenched with water
2. 2
   Extractionextracted three times with dichloromethane
3. 3
   LavageThe combined organic phases are washed with HCl (2M), Na2CO3 (1M)
4. 4
   Séchagea saturated aqueous solution of NaCl, dried over MgSO4
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude product is purified by column chromatography (450 g)
7. 7
   Lavageeluting with a mixture of ethyl acetate and hexane (2:3 to 3:2)

Mode opératoire

DIPEA (15 ml) is added to a solution of N-(tert-butoxycarbonyl)glycine (5.0 g), PYBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate, 16.3 g) and 2,2,2-trifluorethylamine (2.47 ml) in dichloromethane (48 ml). After 24 hours at room temperature, the reaction is quenched with water and extracted three times with dichloromethane. The combined organic phases are washed with HCl (2M), Na2CO3 (1M) and a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified by column chromatography (450 g) eluting with a mixture of ethyl acetate and hexane (2:3 to 3:2) to yield [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-carbamic acid tert-butyl ester (3.89 g).

Source