Reaktion #164558

Reaktionsgleichung

2,2,2-Trifluoroacetic acid

tert-butyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate

Intermediate 7B

tert-butyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate

→

methyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate

Lösungsmittel

dichloromethane

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigebefore leaving
2. 2
   SonstigeThe resultant crude material purified

Vorschrift

2,2,2-Trifluoroacetic acid (3.26 g, 28.0 mmol) was added to a solution of tert-butyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate (Intermediate 7B) (1.0 g, 2.67 mmol) in dichloromethane (20 mL) and methanol (2 mL). The resulting solution was stirred for 7 hours before leaving to stand over the weekend. The resultant crude material purified using a 5 g SCX cartridge to afford methyl 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetate. This was dissolved in tetrahydrofuran (20 mL) and 1M lithium hydroxide solution (5.34 mL, 5.34 mmol) and water (2 mL) was added and the solution stirred overnight. The reaction mixture was then acidified and purified using a 5 g SCX cartridge to afford 2-(2-amino-5-(1,4-diazabicyclo[3.2.2]nonan-4-yl)benzamido)acetic acid (849 mg, 2.67 mmol).

Quelle