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Triethylamine → N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[hydroxy-(1-methyl-2,4-dioxo-pyrrolidin-3-ylidene)-methyl]-benzamide

HRID 2244038
ノート
印刷プレビュー

反応式

HRID 2244038 の反応式
Cl.CO[C:4](=[O:8])[CH2:5][NH:6][CH3:7].[C:9]([C:12]1[CH:46]=[CH:45][C:15]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:44])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32](=[C:34]4C(=O)OC(C)(C)[O:36][C:35]4=O)[OH:33])[CH:27]=3)[CH:21]=[CH:22][CH:23]=2)=[C:14]([CH2:47][CH2:48][CH3:49])[C:13]=1[OH:50])(=[O:11])[CH3:10].C(N(CC)CC)C.[OH-].[K+]>C1(C)C=CC=CC=1.O.CO.O>[C:9]([C:12]1[CH:46]=[CH:45][C:15]([O:16][CH2:17][C:18]2[CH:19]=[C:20]([NH:24][C:25](=[O:44])[C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([OH:33])=[C:34]4[C:4](=[O:8])[CH2:5][N:6]([CH3:7])[C:35]4=[O:36])[CH:27]=3)[CH:21]=[CH:22][CH:23]=2)=[C:14]([CH2:47][CH2:48][CH3:49])[C:13]=1[OH:50])(=[O:11])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 14797Potassium HydroxideHCID 83544Glycine, N-methyl-, methyl ester, hydrochloride (1:1)HCID 54681860N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-benzamide

生成物 1

HCID 68431361N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[hydroxy-(1-methyl-2,4-dioxo-pyrrolidin-3-ylidene)-methyl]-benzamide
収率 8.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 22242641Methanol--water (1/1)溶媒

実験手順

Add sarcosine methyl ester hydrochloride (0.156 g, 1.12 mmol) to a solution of N-[3-(4-acetyl-3-hydroxy-2-propyl-phenoxymethyl)-phenyl]-3-[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-hydroxy-methyl]-benzamide (0.641 g, 1.12 mmol) in toluene (0.2M). Add triethylamine (0.226 g, 2.23 mmol) and heat the solution at reflux for 24 h. Evaporate solvents and add potassium hydroxide (10 mmol) in 1:1 methanol/water (0.2M). Stir the reaction for 24 h. Precipitate product by diluting reaction mixture with water. Filter to afford the title compound (0.050 g, 0.092 mmol, 8%): 1H NMR (400 MHz, DMSO-d6) δ 0.88 (t, J=7.0 Hz, 3H), 1.50 (q, J=9.8 Hz, 2H), 2.57 (s, 3H), 2.61 (t, J=7.2 Hz, 2H), 2.81 (s, 1H), 3.31 (m, 3H), 4.03 (s, 4H)(?), 5.25 (s, 2H), 6.72 (d, J=8.6 Hz, 1H), 7.17 (d, J=7.4 Hz, 1H), 7.37 (t, J=7.8 Hz, 1H), 7.46 (m, 1H), 7.68 (s, 2H), 7.80 (d, J=9.0 Hz, 1H), 7.95 (s, 2H), 8.05 (s, 1H), 10.31 (s, 1H), 12.84 (s, 1H). MS (m/z): 541 (M−1).

後処理

  1. temperatureat reflux for 24 h
  2. customthe reaction for 24 h
  3. additionPrecipitate product by diluting
  4. filtrationFilter

出典と根拠

ORDレコード
ord-cb42baafbba7496a880f1ac542a70486
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678794B2

反応ノート

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