Reaktion #48913

Reaktionsgleichung

4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one

glycine

triethylamine

glycine

triethylamine

→

2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetic acid

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was heated at 75° C. for an additional day
2. 2
   Temperaturto cool to rt
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONdiluted with ethyl acetate (40 mL)
5. 5
   Waschenwashed with 1N HCl (50 mL×3)
6. 6
   SonstigeThe organic layer was dried
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

A mixture of 4-chloro-8-(cyclopentyloxy)-7-methoxy-2H-chromen-2-one (170 mg, 0.58 mmol), glycine (52 mg, 0.69 mmol), triethylamine (0.2 mL, 1.4 mmol), and ethanol (2 mL) was heated at 75° C. in a sealed vial. After 2 d, more glycine (136 mg, 1.8 mmol) and triethylamine (0.3 mL, 2.2 mmol) were added. The reaction was heated at 75° C. for an additional day, allowed to cool to rt, concentrated, diluted with ethyl acetate (40 mL), and then washed with 1N HCl (50 mL×3). The organic layer was dried, filtered, and concentrated to give 2-(8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-ylamino)acetic acid: 1H NMR (400 MHz, DMSO-d6): δ 7.87 (t, 1H), 7.68 (d, 1H), 7.08 (d, 1H), 4.88 (s, 1H), 4.81 (m, 1H), 4.00 (d, 2H), 3.87 (s, 3H), 1.90-1.44 (m, 8H); MS (ESI): 333.9.

Quelle