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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
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HRID 2244038 반응식
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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 22242641Methanol--water (1/1)용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-cb42baafbba7496a880f1ac542a70486
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07678794B2

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