Реакция #1702045

Уравнение реакции

EDCI.HCl

methanesulfonamide

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

→

title compound

Выход 95.7%

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

Выход 95.7%

Растворители

DCM

Условия реакции

Обработка

1. 1
   ДругоеThe ice bath was then removed
2. 2
   Температураto warm to r.t. over night
3. 3
   ДругоеQuenched with citric acid (10% aq.)
4. 4
   Экстракцияextracted with DCM
5. 5
   Сушкаdried over Na2SO4
6. 6
   Концентрированиеconcentrated in vacuo

Методика

(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).

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