Reaktion #2461979

Reaktionsgleichung

TBTU

HCl

(S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid

(S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid tert-butyl ester

2-Methoxyethylamine

DIPEA

→

title compound

Ausbeute 44.9%

(S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid (2-methoxy-ethyl)-amide

Ausbeute 44.9%

Lösungsmittel

DMF CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with CH2Cl2
2. 2
   ExtraktionThe organic layers were subsequently extracted with CH2Cl2 from saturated aqueous NaHCO3
3. 3
   TrocknenThe combined organic phase was dried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by silica gel chromatography

Vorschrift

TBTU (0.077 g), DIPEA (0.090 mL) and (S)-1-[(R)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-5-(4-pyrimidin-5-yl-benzyl)-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid (Example 14) (0.10 g) were combined in 5% DMF-CH2Cl2 (4.2 mL) at room temperature. 2-Methoxyethylamine (0.036 g) was then added and the reaction solution was stirred overnight. The reaction was diluted with CH2Cl2, poured into 1N HCl, and extracted with CH2Cl2. The organic layers were subsequently extracted with CH2Cl2 from saturated aqueous NaHCO3 followed by brine. The combined organic phase was dried (MgSO4), filtered, and concentrated. The residue was purified by silica gel chromatography to afford 0.045 g of the title compound (684.2, M+1) as a foam.

Quelle