Imidazole → HCID 14986680, compound

HRID 1494126Notes

Reaction equation

HRID 1494126 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28]I)[CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:26][CH2:27][CH2:28][N:30]2[CH:34]=[CH:33][N:32]=[CH:31]2)[CH2:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 14986679HCID 14986679, compound

Product 1

HCID 14986680HCID 14986680, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.32 g (0.57 mmol) of t-butyl 8-(p-chlorophenylsulfonamido)-4-(3-iodopropyl)octanoate in 3 mL dry dimethylformamide is added 0.116 g (1.7 mmol) imidazole and the mixture is then refluxed with ethyl acetate and washed with water and brine. The organic layer is dried, filtered, concentrated and then subjected to chromatography using ethyl acetate as eluent to yield t-butyl 8-(p-chloro- phenylsulfonamido)-4-[3-(1-imidazolyl)propyl]octanoate; IR (neat): 1718, 1337, 1164 cm-1 ; NMR (CDCl3): delta 7.5 (br,1H), 7.1 (s,1H), 6.9 (s,1H), 4.2 (t,2H).

Workup

  1. washwashed with water and brine
  2. customThe organic layer is dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92ebb40823bd48b5a6b7d1b380e2b4cb
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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