Quinoline → HCID 10352110, compound

HRID 1155324Notes

Reaction equation

HRID 1155324 reaction equation
[C:1]([O:4]C(=O)C)(=[O:3])[CH3:2].[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11]C=1.[OH-:17].[Na+].N1C2C(=CC=CC=2)C=CC=1>N1C=CC=CC=1>[O:17]=[C:14]1[C@H:13]([O:4][C:1](=[O:3])[CH3:2])[C@H:12]([CH3:11])[O:15][CH:8]=[CH:9]1

Participants

6

Reactant 4

HCID 7047QuinolineHCID 7412Benzoyl chlorideHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 10352110HCID 10352110, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Examples of suitable blocking groups which may be used throughout the present synthesis technique include acetyl ##STR23## and benzoyl ##STR24## groups. These groups may be introduced by reacting the compound of formula 5 with, respectively, such compounds as acetic anhydride or benzoyl chloride. The reaction is preferably conducted in a solvent which is a good acid receptor, such as pyridine, sodium hydroxide solution, or quinoline. Subsequent to the reaction, the solvent is removed under reduced pressure, and the residue is co-evaporated several times with toluene. The product is purified by distillation, recrystallization, and/or column chromatography. When the preferred reactant, acetic anhydride, is reacted with the compound of formula 5, 1,5-anhydro-3-oxo-4-O-acetyl-2,3,6-trideoxy-L-threo-hex-1-enitol is produced.

Workup

  1. custommay be used throughout the present synthesis technique
  2. additionThese groups may be introduced
  3. customSubsequent to the reaction
  4. customthe solvent is removed under reduced pressure
  5. distillationThe product is purified by distillation, recrystallization, and/or column chromatography
  6. customWhen the preferred reactant, acetic anhydride, is reacted with the compound of formula 5

Sources & evidence

ORD record
ord-fbd326e40367481a8d3b59d0cf8c476e
Source dataset
uspto-grants-1981_11
Patent number
US04301276

Reaction notes

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