Reaktion #1715492

Reaktionsgleichung

(S)-1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylic acid

(S)-1-(2-(tert-Butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylic acid

HBTU

DIEA

ammonia

2-propanol

→

(S)-tert-butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Ausbeute 53.0%

(S)-tert-Butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate

Ausbeute 53.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction
2. 2
   Sonstigewas partitioned between 600 ml of EtAc and 200 ml of water
3. 3
   SonstigeThe solvent was removed
4. 4
   Sonstigethe crude purified on a silica gel column (eluting with 10% MeOH in DCM)

Vorschrift

To a 100 ml flask was added (S)-1-(2-(tert-butoxycarbonyl)-3-phenylpropanoyl)-6-(pyridin-4-yl)indoline-4-carboxylic acid 60.A (430 mg, 0.88 mmole), HBTU (669 mg, 1.8 mmole), 20 ml of DMF, DIEA (461 ul, 2.6 mmole) and 2.0 m ammonia solution in 2-propanol (3 ml, 5.3 mmole). The reaction was stirred at 22° C. for 2 hours, at which time the crude reaction was partitioned between 600 ml of EtAc and 200 ml of water. The solvent was removed and the crude purified on a silica gel column (eluting with 10% MeOH in DCM) to give (S)-tert-butyl 1-(4-carbamoyl-6-(pyridin-4-yl)indolin-1-yl)-1-oxo-3-phenylpropan-2-ylcarbamate 60.B as a white solid (228 mg, 53% yield).

Quelle