Реакция #1702046

ord-1415293e8d88416fb053ee83379b3393

Уравнение реакции

O
Water
O=C(n1ccnc1)n1ccnc1
CDI
O=C(O)COc1ccc([C@@H]2CCC(=O)C2)cc1
(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid
[NH4+].[OH-]
Ammonium hydroxide
NC(=O)COc1ccc([C@@H]2CCC(=O)C2)cc1
title compound
Выход 81.0%
NC(=O)COc1ccc([C@@H]2CCC(=O)C2)cc1
2-[4-[(1R)-3-Oxocyclopentyl]phenoxy]acetamide
Выход 81.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Другоеa precipitate formed
  2. 2
    Фильтрацияthe precipitate filtered off
  3. 3
    Другоеdried in vacuo

Методика

(R)-[4-(3-Oxo-cyclopentyl)-phenoxy]-acetic acid (preparation 31) (1.6 mmol, 375 mg) was dissolved in DMF (3 mL), then CDI (1.84 mmol, 299 mg) was added and the reaction mixture stirred at r.t. for 90 min. Ammonium hydroxide (25% aq, 7 mL) was added and a precipitate formed. Water (7 mL) was added and the precipitate filtered off and dried in vacuo to yield the title compound (302 mg, 81%). 1H NMR (300 MHz, CDCl3) δ 7.25-7.14 (m, 2H), 6.97-6.83 (m, 2H), 6.78 (bs, 1H), 5.91 (bs, 1H), 4.49 (s, 2H), 3.52-3.28 (m, 1H), 2.77-2.57 (m, 1H), 2.57-2.11 (m, 5H), 2.09-1.79 (m, 1H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08765676B2uspto-grants-2014_07