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

HRID 2244038Notes

Reaction equation

HRID 2244038 reaction equation
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]

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-cb42baafbba7496a880f1ac542a70486
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

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