تفاعل #1702046

ord-1415293e8d88416fb053ee83379b3393

معادلة التفاعل

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

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىa precipitate formed
  2. 2
    ترشيحthe precipitate filtered off
  3. 3
    أخرىdried in vacuo

الإجراء التجريبي

(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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08765676B2uspto-grants-2014_07