HCID 21474275, compound → HCID 21474471, compound

HRID 2294268Notes

Reaction equation

HRID 2294268 reaction equation
C([O:8][C:9]1[C:10](=[O:27])[CH:11]=[CH:12][N:13]2[CH2:18][CH:17]([O:19][CH3:20])[O:16][CH:15]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:14]=12)C1C=CC=CC=1.C(OC1C(=O)C=CN(CC(OC)OC)C=1C(C1C=CC=CC=1)OC1CCCCO1)C1C=CC=CC=1.C(OCC)(=O)C.C(O)C>CO.Cl>[OH:8][C:9]1[C:10](=[O:27])[CH:11]=[CH:12][N:13]2[CH2:18][CH:17]([O:19][CH3:20])[O:16][CH:15]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:14]=12

Participants

6

Reactant 3

HCID 21474275HCID 21474275, compound2×HCID 21474371HCID 21474371, compoundHCID 21584252Ethanol ethylacetate

Product 1

HCID 21474471HCID 21474471, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

9-Benzyloxy-3-methoxy-1-phenyl-3,4-dihydro-1H-pyrido[2,1-c][1,4]oxazin-8-one: 2.13 g of 3-benzyloxy-1-(2,2-dimethoxy-ethyl)-2-[phenyl-(tetrahydro-pyran-2-yloxy)-methyl]-1H-pyridin-4-one are boiled under reflux for 2 hours in 5 ml of methanol and 8.8 ml of 2N hydrochloric acid. The methanol is distilled off using a rotary evaporator and the residue is diluted with water and neutralised with 8.8 ml of 2N sodium hydroxide solution. Extraction is carried out with ethyl acetate and the extracts are washed twice with water. The extracts are dried, filtered and concentrated by evaporation. Chromatography yields: 1.3 g of 9-benzyloxy-3-methoxy-1-phenyl-3,4-dihydro-1H-pyrido[2,1-c][1,4]oxazin-8-one in the form of a diastereoisomeric mixture. Yellow resin. Rf value: 0.45 (silica gel 60, ethyl acetate/ethanol 9/1).

Workup

  1. distillationThe methanol is distilled off
  2. customa rotary evaporator
  3. additionthe residue is diluted with water and neutralised with 8.8 ml of 2N sodium hydroxide solution
  4. extractionExtraction
  5. washthe extracts are washed twice with water
  6. customThe extracts are dried
  7. filtrationfiltered
  8. concentrationconcentrated by evaporation
  9. customChromatography yields

Sources & evidence

ORD record
ord-72677ca25d834477b88768021fbeb043
Source dataset
uspto-grants-1997_11
Patent number
US05688815

Reaction notes

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