Reaktion #77838

Reaktionsgleichung

2-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid

pyrrolidine

HCl

4-methylmorpholine

glycine benzyl ester hydrogen chloride

BOP Reagent

→

glycine

N-[2-[(1-Pyrrolidinylcarbonyl)amino]-5-(trifluoromethyl)benzoyl]glycine

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine
2. 2
   TrocknenThe EtOAc was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated to a solid (2.6 g)
5. 5
   workup.DISSOLUTIONThis solid was dissolved in MeOH (14 mL)
6. 6
   workup.ADDITIONto the addition of 10% Pd/C
7. 7
   workup.ADDITIONA hydrogen balloon was added
8. 8
   workup.STIRRINGthe solution was stirred for 1 h
9. 9
   FiltrationThe palladium was filtered
10. 10
    Einengenthe solution was concentrated

Vorschrift

2-(Pyrrolidinylcarbonyl)amino-5-trifluoromethylbenzoic acid (made analogously to Example 116 with pyrrolidine in place of iso-butylamine (2.9 g) was dissolved in DMF (40 mL). After cooling to 0° C., 4-methylmorpholine (3.2 mL) and glycine benzyl ester hydrogen chloride (5.6 g) were added. After 5 min, BOP Reagent (5.6 g) was added and the mixture was stirred at rt for 18 h. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl, NaHCO3 solution, and brine. The EtOAc was dried (MgSO4), filtered, and concentrated to a solid (2.6 g). This solid was dissolved in MeOH (14 mL) prior to the addition of 10% Pd/C. A hydrogen balloon was added and the solution was stirred for 1 h. The palladium was filtered and the solution was concentrated to give the title glycine derivative (2.0 g) as a white solid. MS found: (M+H)+=360.2.

Quelle