Réaction #1702045

Équation de réaction

EDCI.HCl

methanesulfonamide

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

→

title compound

Rendement 95.7%

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

Rendement 95.7%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe ice bath was then removed
2. 2
   Températureto warm to r.t. over night
3. 3
   AutreQuenched with citric acid (10% aq.)
4. 4
   Extractionextracted with DCM
5. 5
   Séchagedried over Na2SO4
6. 6
   Concentrationconcentrated in vacuo

Mode opératoire

(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).

Source