تفاعل #1702045

معادلة التفاعل

EDCI.HCl

methanesulfonamide

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

→

title compound

المردود 95.7%

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

المردود 95.7%

المذيبات

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice bath was then removed
2. 2
   درجة الحرارةto warm to r.t. over night
3. 3
   أخرىQuenched with citric acid (10% aq.)
4. 4
   استخلاصextracted with DCM
5. 5
   تجفيفdried over Na2SO4
6. 6
   تركيزconcentrated in vacuo

الإجراء التجريبي

(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).

المصدر