Hydrochloric Acid → HCID 21263786, compound

HRID 566861Notes

Reaction equation

HRID 566861 reaction equation
[CH3:1][C:2]1O[CH:4]=[CH:5][C:6](=[O:16])[C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(O)C.O.Cl.C[C:23]1[NH:24]C=C[C:27](=[O:37])[C:28]=1[O:29]CC1C=CC=CC=1>OCC(CO)O>[CH2:23]([N:24]1[CH:4]=[CH:5][C:6](=[O:16])[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:2]1[CH3:1])[CH:28]([CH2:27][OH:37])[OH:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14901193-Benzyloxy-2-methyl-4-pyroneHCID 27264163-(BENZYLOXY)-2-METHYL-4(1H)-PYRIDINONEHCID 19096565Water ethanol

Product 1

HCID 21263786HCID 21263786, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

35.6 g (165 mmol. 1.5 eq.) of 2-methyl-3-benzyloxy-4-pyranone and 10 g (110 mmol) of 1-amino-1-desoxy-glycerol are put into 600 mL of a 50:50 ethanol-water mixture; then 14 mL of an aqueous solution of soda (2N) is added. The reaction medium is then brought under reflux agitation for 48 hours. The reaction medium is left to cool, and then a solution of concentrated HCl is added to reach a pH=1. After evaporation of ethanol, the resifue is extracted using ethyl ether (3×100 mL) in order to eliminate any excess of 2-methyl-3-benzyloxy-4-pyranone. The aqueous phase is brought to neutral pH by addition of an aqueous solution of NaOH and then concentrated under reduced pressure. The residue is retaken up with a minimum of water. By precipitation, 12.7 g (43.9 mmol) of 2-methyl-3-benzyloxypyridine-4(1H)-one of glycerol is isolated, which is pure at chromatographic and NMR analyses. Yield 40%.

Workup

  1. temperatureunder reflux agitation for 48 hours
  2. waitThe reaction medium is left
  3. temperatureto cool
  4. customAfter evaporation of ethanol
  5. extractionthe resifue is extracted
  6. additionThe aqueous phase is brought to neutral pH by addition of an aqueous solution of NaOH
  7. concentrationconcentrated under reduced pressure
  8. customis isolated

Sources & evidence

ORD record
ord-96911ea297764b519ea8aeb818a9b0a8
Source dataset
uspto-grants-2001_01
Patent number
US06177409B1

Reaction notes

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