Reaktion #606239

Reaktionsgleichung

3-methyl-3-[4-methyl-3-oxo-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-azetidine-1-carboxylic acid tert-butyl ester

TBAF

→

(R)-tert-butyl 3-methyl-3-((1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate

Ausbeute 19.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to ambient temperature
2. 2
   Sonstigesolvent was removed in vacuo
3. 3
   SonstigeThe residue was purified by preparative HPLC (Table 3, Method 17)
4. 4
   Sonstigefurther separated by chiral SFC (Table 2, Method 10)

Vorschrift

To a solution of 3-methyl-3-[4-methyl-3-oxo-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-ylamino]-azetidine-1-carboxylic acid tert-butyl ester (4 g, 6.67 mmol) in THF (10 mL) was added a solution of TBAF (1M in THF, 80 mL, 80 mmol) The reaction mixture was heated at 80° C. for 15 h. The reaction mixture was cooled to ambient temperature and solvent was removed in vacuo. The residue was purified by preparative HPLC (Table 3, Method 17) and further separated by chiral SFC (Table 2, Method 10) to give (R)-tert-butyl 3-methyl-3-((1-methyl-2-oxo-8-(trifluoromethyl)-1,2,3,5-tetrahydrobenzo[5,6][1,4]oxazino[3,4-c][1,2,4]triazin-9-yl)amino)azetidine-1-carboxylate (Enantiomer 1, SFC (Table 1, Method 16) Rt: 6.686 min, 0.600 g, 19%) as a white solid, LC/MS (Table 1, Method 2) Rt=1.192 min.; MS m/z: 492 [M+23]+.

Quelle