Thiazole → HCID 131716223, compound

HRID 329498Notes

Reaction equation

HRID 329498 reaction equation
[CH2:1]([NH:18][C:19]([S:21][C@H:22]1[CH2:27][CH2:26][CH2:25][O:24][C@H:23]1[CH2:28][O:29][C:30](=[O:38])[NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][Br:37])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[S:39]1[CH:43]=[CH:42][N:41]=[CH:40]1>C1(C)C=CC=CC=1>[Br-:37].[CH2:1]([NH:18][C:19]([S:21][C@H:22]1[CH2:27][CH2:26][CH2:25][O:24][C@H:23]1[CH2:28][O:29][C:30]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N+:41]1[CH:42]=[CH:43][S:39][CH:40]=1)=[O:38])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 9256ThiazoleHCID 18637138HCID 18637138, compound

Product 1

HCID 131716223HCID 131716223, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

600 mg of dl-[cis-3-(N-heptadecylcarbamoylthio)tetrahydropyran-2-ylmethyl]N-(5-bromopentyl)carbamate (prepared as described in Preparation 42) were dissolved in 1 ml of toluene, and then 0.68 ml of thiazole were added to the resulting mixture. The mixture was then heated on an oil bath kept at 80° C. for 64 hours. At the end of this time, the reaction mixture was evaporated to dryness under reduced pressure, and the residue was subjected to column chromatography through 15 g of silica gel. 595 mg of the title compound were obtained as a white powder, melting at 122°-125° C., from the fractions eluted with mixtures of methylene chloride and methanol ranging from 9:1 to 4:1 by volume.

Workup

  1. temperatureThe mixture was then heated on an oil bath
  2. customAt the end of this time, the reaction mixture was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-44558aa8f7d442608f2b3f5a540a60c9
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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