Reaktion #166700

Reaktionsgleichung

(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate

THF

LiOH

→

(R)-4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid

Ausbeute 24.4%

Lösungsmittel

water

MeOH

MeOH

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with DCM
2. 2
   SonstigeThe combined organic fractions were dried
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   Sonstigeto give a crude residue
6. 6
   SonstigeThe residue was purified by column

Vorschrift

(R)-Methyl 4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (0.210 g, 0.3874 mmol, see Example 2) was placed in 2:1 THF:MeOH (6 mL). 3M LiOH (aq., 1.29 mL, 3.87 mmol) was then added, and the reaction was heated to 65° C. for 2 hours. The reaction was then diluted with water and extracted with DCM. The combined organic fractions were dried, filtered, and concentrated to give a crude residue. The residue was purified by column:chromatography (20:1 DCM:MeOH) to give (R)-4-(4-(2-(tert-butoxycarbonylamino)-3-(4-chlorophenyl)propanoyl)piperazin-1-yl)-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid (0.050 g, 24.4% yield).

Quelle