Reaktion #1462261

Reaktionsgleichung

[1-(4-amino-phenyl)-cyclopentyl]-acetic acid tert-butyl ester

O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate

[3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid

diisopropylethylamine

→

title compound

[1-{4-[2-[3-Methoxy-4-[3-o-tolyl-ureido]-phenyl]-acetylamino]-phenyl}-cyclopentyl]-acetic acid tert-butyl ester

Lösungsmittel

dimethylformamide

dimethylformamide

methanol

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas stirred at room temperature for 2 hours
2. 2
   Sonstigeevaporated to low bulk
3. 3
   SonstigeThe residue was partitioned between water (containing 1 mL of 1M hydrochloric acid solution) and ethyl acetate
4. 4
   WaschenThe organic phase was washed with water
5. 5
   Trocknenwith brine, then dried over magnesium sulfate
6. 6
   Sonstigeevaporated
7. 7
   Sonstigeto yield a fawn solid which

Vorschrift

A stirred solution of [3-methoxy-4-(3-o-tolyl-ureido)-phenyl]-acetic acid (0.26 g, prepared as described in Example 52 of International Patent Application Publication No. WO 96/22966) in dry dimethylformamide (15 mL), under argon, was treated with O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (0.32 g). This solution was stirred at room temperature for 10 minutes and then treated with diisopropylethylamine (0.28 ml) and a solution of [1-(4-amino-phenyl)-cyclopentyl]-acetic acid tert-butyl ester (0.21 g, Reference Example 5a) in dry dimethylformamide (5 mL). The resulting amber coloured solution was stirred at room temperature for 2 hours and then evaporated to low bulk. The residue was partitioned between water (containing 1 mL of 1M hydrochloric acid solution) and ethyl acetate. The organic phase was washed with water, then with brine, then dried over magnesium sulfate and then evaporated to yield a fawn solid which was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (49:1, v/v) to give the title compound (0.30 g) as a pale yellow solid. MS(ES+): 594(M+Na)+; MS (ES−): 570 (M−H).

Quelle