Imidazole → HCID 67906936, compound

HRID 982476Notes

Reaction equation

HRID 982476 reaction equation
[OH:1][CH:2]([CH3:39])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[O:23]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20]Br)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[NH:40]1[CH:44]=[CH:43][N:42]=[CH:41]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][CH:2]([CH3:39])[CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:22]2[CH2:26][CH2:25][C@H:24]([C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[C:29]([O:37][CH3:38])[CH:28]=3)[O:23]2)[CH:10]=[C:11]([O:17][CH2:18][CH2:19][CH2:20][N:40]2[CH:44]=[CH:43][N:42]=[CH:41]2)[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 15078313HCID 15078313, compound

Product 1

HCID 67906936HCID 67906936, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(3-bromopropoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (87 mg, 0.14 mmol) (Example 19B), imidazole (47 mg, 0.69 mmol) and potassium carbonate (95 mg, 0.69 mmol) in acetone (2 mL) was heated with stirring at 55° C. under nitrogen for 28 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; 9:1, v/v) gave the title compound: Rf 0.6; MS, m/z 618 M+. ; NMR (CDCl3) δ 1.28 (bd, CH2CHOHCH3), 6.94 and 7.08 (bs, NCH=CHN), 7.54 (NCH=N).

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-77bfdda936324e218cab3851b77fbf84
Source dataset
uspto-grants-1991_02
Patent number
US04996203

Reaction notes

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