반응 #1702045

반응 방정식

EDCI.HCl

methanesulfonamide

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

→

title compound

수율 95.7%

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

수율 95.7%

용매

DCM

반응 조건

후처리

1. 1
   기타The ice bath was then removed
2. 2
   온도to warm to r.t. over night
3. 3
   기타Quenched with citric acid (10% aq.)
4. 4
   추출extracted with DCM
5. 5
   건조dried over Na2SO4
6. 6
   농축concentrated in vacuo

실험 절차

(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).

출처