Dimethylformamide → 3-(4-{2-[1-(4-Hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester

HRID 1985262노트

반응식

HRID 1985262 반응식
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:14][CH:15]([CH3:17])[CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[CH3:19][N:20]1[CH:24]([CH2:25][CH2:26]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:23][N:22]([CH2:38][C:39]2[CH:44]=[CH:43][C:42](C(F)(F)F)=[CH:41][CH:40]=2)[C:21]1=[O:49].CN(C=[O:54])C>>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:14][CH:15]([CH3:17])[CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:26][CH2:25][CH:24]2[CH2:23][N:22]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([OH:54])=[CH:41][CH:40]=3)[C:21](=[O:49])[N:20]2[CH3:19])=[CH:11][CH:12]=1)[CH3:2]

참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 22926879Ethyl 3-(4-hydroxyphenyl)-2-isopropoxypropanoateHCID 86596229HCID 86596229, 화합물

생성물 1

HCID 688699793-(4-{2-[1-(4-Hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester수율 67%

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온도
65 °C

실험 절차

A mixture of 3-(4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl ester (0.034 g, 0.134 mmol), toluene-4-sulfonic acid 2-[3-methyl-2-oxo-1-(4-trifluoromethyl-benzyl)-imidazolidin-4-yl]-ethyl ester (0.068 g, 0.149 mmol) and CS2CO3 (0.066 g, 0.202 mmol) in DMF (6 mL) was heated to 65° C. under N2 for 16 h. The reaction was cooled and quenched with 1 N HCl (10 mL) and worked up extractively with Et2O and water. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford crude product that was purified by flash chromatography using 4:1 hexanes:acetone to afford 0.048 g (67%) 3-(4-{2-[1-(4-hydroxy-benzyl)-3-methyl-2-oxo-imidazolidin-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester. Rf=0.36 (1:1 hexanes:acetone). 1H NMR (500 MHz, CDCl3)δ 1H NMR (500 MHz, CDCl3) □ 7.56 (d, 2H, J=8.07 Hz), 7.36 (d, 2H, J=8.07 Hz), 7.13 (d, 2H, J=8.80 Hz), 6.72 (d, 2H, J=8.80 Hz), 4.47, 4.36 (ABq, 2H, J=15.16 Hz), 4.20-4.12 (m, 2H), 4.00-3.94 (m, 3H), 3.66-3.59 (m, 1H), 3.48 (hp, 1H, J=5.87 Hz), 3.37 (t, 1H, J=8.80 Hz), 2.98 (t, 1H, J=8.80 Hz), 2.90-2.85 (m, 2H), 2.84 (s, 3H), 2.27-2.23 (m, 1H), 1.93-1.84 (m, 1H), 1.23 (t, 3H, J=6.85 Hz), 1.14 (d, 3H, J=5.87 Hz), 0.97 (d, 3H, J=5.87 Hz). MS (ES+) Calc'd for C28H36N2O5F3 (M+1) 537. Found m/z 537 (100%).

후처리

  1. temperatureThe reaction was cooled
  2. customquenched with 1 N HCl (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthe solvent removed in vacuo
  5. customto afford crude product that
  6. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-9b1aebe368074a73b5f44adfff987e86
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544812B2

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