Imidazole → HCID 67906915, compound

HRID 1196704Notes

Reaction equation

HRID 1196704 reaction equation
[OH:1][CH:2]([CH3:40])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21]Br)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[NH:41]1[CH:45]=[CH:44][N:43]=[CH:42]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][CH:2]([CH3:40])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:23]2[CH2:27][CH2:26][C@H:25]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[C:31]([O:36][CH3:37])=[C:30]([O:38][CH3:39])[CH:29]=3)[O:24]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][N:41]2[CH:45]=[CH:44][N:43]=[CH:42]2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 15078314HCID 15078314, compound

Product 1

HCID 67906915HCID 67906915, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trans-2-[-3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(4-bromobutoxy)phenyl]-5-(3,4,5-trimethoxyphenyl) tetrahydrofuran (64 mg, 0.10 mmol)(Example 19C), imidazole (27 mg, 0.40 mmol) and potassium carbonate (55 mg, 0.40 mmol) in acetone (3 mL) was heated with stirring at 60° C. under nitrogen for 24 h. The reaction mixture was evaporated and the residue was partitioned between dichloromethane and water. The organic layer was washed with water and brine, dried, and evaporated to a residue. Purification by preparative TLC (CH2Cl2 -MeOH; 92.8, v/v) gave the title compound: Rf 0.5; MS, m/z 632 M+. ; NMR (CDCl3) δ 1.28 (bd, CH2CHOHCH3), 6.94 & 7.08 (bs, NCH=CHN).

Workup

  1. temperaturewas heated
  2. customThe reaction mixture was evaporated
  3. customthe residue was partitioned between dichloromethane and water
  4. washThe organic layer was washed with water and brine
  5. customdried
  6. customevaporated to a residue
  7. customPurification by preparative TLC (CH2Cl2 -MeOH

Sources & evidence

ORD record
ord-dc2a700ad44643189c880328c5e9b3fc
Source dataset
uspto-grants-1992_05
Patent number
US05114961

Reaction notes

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