反応 #1702046

ord-1415293e8d88416fb053ee83379b3393

反応方程式

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
収率 81.0%
NC(=O)COc1ccc([C@@H]2CCC(=O)C2)cc1
2-[4-[(1R)-3-Oxocyclopentyl]phenoxy]acetamide
収率 81.0%

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他a precipitate formed
  2. 2
    ろ過the precipitate filtered off
  3. 3
    その他dried in vacuo

実験手順

(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).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08765676B2uspto-grants-2014_07