Thiazole → HCID 13457515, compound

HRID 1285240Notes

Reaction equation

HRID 1285240 reaction equation
[P:1]([O-:35])([O:31][CH2:32][CH2:33]Br)([O:3][CH2:4][CH:5]([O:29][CH3:30])[CH2:6][O:7][C:8](=[O:28])[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][CH2:26][CH3:27])=[O:2].[S:36]1[CH:40]=[CH:39][N:38]=[CH:37]1>>[P:1]([O-:35])([O:31][CH2:32][CH2:33][C:37]1[S:36][CH:40]=[CH:39][NH+:38]=1)([O:3][CH2:4][CH:5]([O:29][CH3:30])[CH2:6][O:7][C:8](=[O:28])[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][CH2:26][CH3:27])=[O:2]

Participants

3

Reactant 2

HCID 9256ThiazoleHCID 131713133HCID 131713133, compound

Product 1

HCID 13457515HCID 13457515, compound

Conditions

Temperature
60 °C

Procedure

A mixture of 2.0 g of the phosphate ester obtained in Example 10 and 4.5 g of thiazole is stirred and warmed at 60° C. for 5 days. The thiazole is distilled off under reduced pressure, and 50 ml of methanol and 2 g of silver carbonate are added to the residue. The mixture is heated under reflux for 2 hours. After filtration, the filtrate is evaporated to dryness, and the residue is separated and purified by silica gel chromatography [eluent: chloroform-methanol-water (65:25:4)] and crystallized from chloroform-acetone to obtain the contemplated product.

Workup

  1. distillationThe thiazole is distilled off under reduced pressure, and 50 ml of methanol and 2 g of silver carbonate
  2. additionare added to the residue
  3. temperatureThe mixture is heated
  4. temperatureunder reflux for 2 hours
  5. filtrationAfter filtration
  6. customthe filtrate is evaporated to dryness
  7. customthe residue is separated
  8. custompurified by silica gel chromatography [eluent: chloroform-methanol-water (65:25:4)]
  9. customcrystallized from chloroform-acetone
  10. customto obtain the contemplated product

Sources & evidence

ORD record
ord-ccf0731ebd8b475b9984371b73163287
Source dataset
uspto-grants-1986_01
Patent number
US04565865

Reaction notes

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