Reaktion #79819

Reaktionsgleichung

3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclopentanol

2-[(tert-butoxycarbonyl)amino]acetic acid

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

→

3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-[(tert-butoxycarbonyl)amino]acetate

Ausbeute 55.8%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe mixture was pour onto ice-water
2. 2
   ExtraktionThe aqueous layer was extracted with ethyl acetate three times
3. 3
   WaschenThe combined organic layer was washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated
7. 7
   SonstigeThe residue was purified by flash column chromatography

Vorschrift

A mixture of 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-1-cyclopentanol (50 mg, 0.129 mmol), 2-[(tert-butoxycarbonyl)amino]acetic acid (34 mg, 0.194 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (31 mg, 0.155 mmol) and 4-(dimethylamino)pyridine (16 mg, 0.129 mmol) in DMF (1 mL) was stirred under nitrogen for 24 hours. The mixture was pour onto ice-water. The aqueous layer was extracted with ethyl acetate three times. The combined organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The residue was purified by flash column chromatography using ethyl acetate as mobile phase to give 3-[4-amino-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl 2-[(tert-butoxycarbonyl)amino]acetate (39 mg, 0.072 mmol). HPLC: tr=19.22 min. (Delta-Pack, C-18, 5 μm, 300 A, 3.9×150 mm; 5-85% acetonitrile—0.1 M ammonium acetate over 20 min, 1 ml/min).

Quelle