Methanol → HCID 9863371, compound

HRID 1018482Notes

Reaction equation

HRID 1018482 reaction equation
[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[O:4][NH:3]1.[CH3:17][O:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1.C(N=C=NCCCN(C)C)C.CO>ClCCl.CN(C)C=O.C(#N)C>[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH:5]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[O:4][N:3]1[C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([O:18][CH3:17])=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 887Methanol2×HCID 74784-Methoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18401526HCID 18401526, compound

Product 1

HCID 9863371HCID 9863371, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.75 ml of a 0.05M solution of 3,5-dimethyl-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine in dichloromethane, 0.5 ml of a 0.05M solution of 4-methoxybenzoic acid in dimethylformamide, and 0.5 ml of a 0.075M solution of N-ethyl-N′-dimethylaminopropyl-carbodiimide hydrochloroide in acetonitrile was stirred at ambient temperature for 18 h. Methanol (1 ml) was added with stirring and the mixture applied to a methanol washed 500 mg Isolute SCX cartridge (Jones Chromatography). The absorbent was then washed with methanol (2.5 ml) and the combined run through and washing concentrated to dryness using a centrifugal evaporator. The residue was dissolved in ethyl acetate (0.5 ml) and applied to a 100 mg Isolute SI cartridge (Jones Chromatography). Elution with ethyl acetate (2 ml) followed by removal of the solvent by centrifugal evaporation gave 3,5-dimethyl-2-(4-methoxybenzoyl)-6-(4-methoxyphenyl)-3,6-dihydro-2H-1,2-oxazine.

Workup

  1. stirringwith stirring
  2. washwashed 500 mg Isolute SCX cartridge (Jones Chromatography)
  3. washThe absorbent was then washed with methanol (2.5 ml)
  4. washthe combined run through and washing
  5. concentrationconcentrated to dryness
  6. customa centrifugal evaporator
  7. dissolutionThe residue was dissolved in ethyl acetate (0.5 ml)
  8. washElution with ethyl acetate (2 ml)
  9. customfollowed by removal of the solvent by centrifugal evaporation

Sources & evidence

ORD record
ord-970a66eaa7ad4397af1a8905b8eef7db
Source dataset
uspto-grants-2002_11
Patent number
US06482824B1

Reaction notes

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