Thiazole → HCID 131717087, compound

HRID 974677Notes

Reaction equation

HRID 974677 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].[S:39]1[CH:43]=[CH:42][N:41]=[CH:40]1>C1(C)C=CC=CC=1>[P:1]([O-:38])([O:34][CH2:35][CH2:36][C:40]1[S:39][CH:43]=[CH:42][NH+: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 9256ThiazoleHCID 19986121HCID 19986121, compound

Product 1

HCID 131717087HCID 131717087, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 0.940 g of (2RS)-3-(N-heptadecylcarbamoyloxy)-2-(3-isoxazolyloxy)propyl 2-bromoethyl phosphate [prepared as described in Example 11(a)] and 1.06 ml of thiazole in toluene was heated on an oil bath kept at 70° C. for 4 days, whilst stirring. The solvent 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 solution thus obtained was passed over 11 ml of Amberlite (trade mark) MB 3 resin. The eluate was repeatedly passed six 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. 0.312 g of the title compound was obtained as a resinous material from the fractions eluted with a 60:35:5 by volume mixture of methylene chloride, methanol and water.

Workup

  1. distillationThe solvent was then distilled off
  2. dissolutionthe resulting residue was dissolved in 10 ml of a 95:5 by volume mixture of tetrahydrofuran and water
  3. customThe solution thus obtained
  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-b620247198864ec2847dfcd87bb9ed84
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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