1-Methylimidazole → HCID 178443007, compound

HRID 974678Notes

Reaction equation

HRID 974678 reaction equation
[P:1]([O-:38])([O:34][CH2:35][CH2:36]Br)([O:3][CH2:4][CH:5]([O:28][C:29]1[CH:33]=[CH:32][O:31][N:30]=1)[CH2:6][O:7][C:8](=[O:27])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:2].[CH3:39][N:40]1[CH:44]=[CH:43][N:42]=[CH:41]1>C1(C)C=CC=CC=1>[P:1]([O-:38])([O:34][CH2:35][CH2:36][N+:42]1[CH:43]=[CH:44][N:40]([CH3:39])[CH:41]=1)([O:3][CH2:4][CH:5]([O:28][C:29]1[CH:33]=[CH:32][O:31][N:30]=1)[CH2:6][O:7][C:8](=[O:27])[NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:2]

Participants

4

Reactant 2

HCID 13901-MethylimidazoleHCID 19986121HCID 19986121, compound

Product 1

HCID 178443007HCID 178443007, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.900 g of (2RS)-3-(N-heptadecylcarbamoyloxy)-2-(3-isoxazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in Example 11(a)], 1.14 ml of N-methylimidazole and 1.0 ml of toluene was heated on an oil bath kept at 80° C. for 15 hours, whilst stirring. The toluene was then distilled off, and the resulting residue was dissolved in 10 ml of a 95:5 by volume mixture of tetrahydrofuran and water. The resulting solution was passed through a column of 14 ml of Amberlite MB-3 resin. The eluate wa repeatedly passed two times through the same column and the column was finally washed with a 95:5 by volume mixture of tetrahydrofuran and water. The eluates and the washings were combined and concentrated by evaporation under reduced pressure. The residue was purified by medium pressure liquid chromatography using a Lobar B column. 0.656 g of the title compound was obtained as a white powder melting at 45°-46° C. from the fractions eluted with a 160:35:5 by volume mixture of methylene chloride, methanol and water.

Workup

  1. temperaturewas heated on an oil bath
  2. distillationThe toluene was then distilled off
  3. dissolutionthe resulting residue was dissolved in 10 ml of a 95:5 by volume mixture of tetrahydrofuran and water
  4. washthe column was finally washed with a 95:5 by volume mixture of tetrahydrofuran and water
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was purified by medium pressure liquid chromatography

Sources & evidence

ORD record
ord-ac76a62f9ae54128b63dd2c8f9c459fd
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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