Dicyclohexylcarbodiimide → HCID 54213439、化合物

HRID 439878ノート

反応式

HRID 439878 の反応式
[O:1]1[CH:5]=[CH:4][C:3]([CH:6]([N:8]([OH:12])[C:9]([NH2:11])=[O:10])[CH3:7])=[CH:2]1.[CH3:13][C@H:14]([C:27](O)=[O:28])[C:15]1[CH:16]=[CH:17][C:18]2[CH:19]=[C:20]([O:25][CH3:26])[CH:21]=[CH:22][C:23]=2[CH:24]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:26][O:25][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[CH:24]=[C:15]([C@H:14]([CH3:13])[C:27]([O:12][N:8]([CH:6]([C:3]1[CH:4]=[CH:5][O:1][CH:2]=1)[CH3:7])[C:9]([NH2:11])=[O:10])=[O:28])[CH:16]=[CH:17]2

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 130007N-1-(fur-3-ylethyl)-N-hydroxyureaHCID 156391Naproxen

生成物 1

HCID 54213439HCID 54213439、化合物収率 68.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-1-(fur-3-yl)ethyl-N-hydroxyurea (1.00 g, 5.9 mmol), prepared as described in U.S. Pat. No. 5,112,848, in CH2Cl2 (25 mL) was added naproxen (135 g, 5.9 mmol) followed by dicyclohexylcarbodiimide (1.34 g, 6.49 mmol), and a crystal of 4-N,N-dimethylaminopyridine. The reaction was stirred for 18 hours. The reaction mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (ether), followed by crystallization in ethyl acetate/hexanes to give N-[(S)-2-(6-methoxynaphth-2-yl)propionyloxy]-N-[1-(fur-3-yl)ethyl]urea (1.54 g). m.p. 128.5°-134° C. 1H NMR (300 MHz, DMSO-d6, mixture of diastereomers) δ 0.72 and 1.12 (bm, 3H), 1.48 (bm, 3H), 3.87 (s, 3H), 4.13 (bm, 1H), 5.14 (bm, 1H), 6.79 and 6.94 (bs, 2H), 7.16 (m, 2H), 7.29-7.46 (m, 3H), 7.69-7.86 (m, 3H). MS (DCI/NH3) m/e 383 (M+H)+. Analysis calc'd for C21H22N2O5 : C, 65.95; H, 5.80; N, 7.33. Found: C, 65.39; H; 5.80; N, 7.26.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (ether)
  4. customfollowed by crystallization in ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-bd02401f04754aee997b55f1a6417696
出典データセット
uspto-grants-1996_05
特許番号
US05516789

反応ノート

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