Reaktion #1702045

Reaktionsgleichung

EDCI.HCl

methanesulfonamide

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid

→

title compound

Ausbeute 95.7%

N-Methylsulfonyl-2-[4-[(1R)-3-oxocyclopentyl]phenoxy]acetamide

Ausbeute 95.7%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was then removed
2. 2
   Temperaturto warm to r.t. over night
3. 3
   SonstigeQuenched with citric acid (10% aq.)
4. 4
   Extraktionextracted with DCM
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated in vacuo

Vorschrift

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (2.5 mmol, 585 mg) was dissolved in DCM (30 mL) and cooled to 0° C. on an icebath. EDCI.HCl (3.75 mmol, 720 mg), methanesulfonamide (2.75 mmol, 261 mg) and DMAP (3.75 mmol, 458 mg) was added and the reaction mixture left an additional 15 min on the ice bath. The ice bath was then removed and the reaction was allowed to warm to r.t. over night. Quenched with citric acid (10% aq.) and extracted with DCM, then dried over Na2SO4 and concentrated in vacuo to yield the title compound (745 mg, 95%). 1H NMR (300 MHz, CDCl3) δ 8.84 (bs, 1H), 7.25-7.19 (m, 2H), 6.95-6.85 (m, 3H), 4.58 (s, 2H), 3.58-3.08 (m, 5H), 2.78-2.58 (m, 1H), 2.58-2.15 (m, 5H), 2.15-1.78 (m, 1H).

Quelle