Reaktion #7767

Reaktionsgleichung

BOP Reagent

Hunig's base

2-(tert-butoxycarbonyl)amino-5-trifluoromethylbenzoic acid

Glycine benzyl ester p-toluenesulfonate salt

HCl

→

acetic acid benzyl ester

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting mixture was warmed to rt
2. 2
   WaschenThe EtOAc layer was washed with 1 N HCl (aq), NaHCO3 solution (aq), and brine
3. 3
   TrocknenThe EtOAc was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated

Vorschrift

Glycine benzyl ester p-toluenesulfonate salt (6.03 g) was dissolved in DMF prior to the addition of Hunig's base (12.4 mL) and 2-(tert-butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6 g) (Takagishi et al., Synlett 1992, 360). After cooling to 0° C., BOP Reagent (8.69 g) was added. The resulting mixture was warmed to rt and was stirred 96 h. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl (aq), NaHCO3 solution (aq), and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave 2-tert-butoxycarbonylamino-5-trifluoromethyl-benzoylamino)-acetic acid benzyl ester (5.78 g). MS found: (M+Na)+=475.3.

Quelle