HCID 19354581, compound → HCID 19354605, compound

HRID 377565Notes

Reaction equation

HRID 377565 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:29])[C:11]([N:14]1[C:19](=[O:20])[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([CH2:27][OH:28])[O:16][CH2:15]1)([CH3:13])[CH3:12].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[NH:9][C:10](=[O:29])[C:11]([N:14]1[C:19](=[O:20])[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([CH:27]=[O:28])[O:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 19354581HCID 19354581, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 19354605HCID 19354605, compoundYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-hydroxymethyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (1.0 g) in dichloromethane was added to a stirred mixture of pyridinium chlorochromate (0.8 g) and powdered 4A molecular sieve (1.6 g) in dichloromethene. After 2 hours the mixture was purified directly by dry column chromatography on silica gel, eluting with dichloromethane to give N-(2,5-difluorophenyl)-2-(2,3-dihydro-6-formyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methylpropanamide (compound 129, 0.83 g) as a pale green solid, m.p. 76-77.5° C.

Workup

  1. customAfter 2 hours the mixture was purified directly
  2. customby dry column chromatography on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0044caa15f8e433296ca72ba936abb4a
Source dataset
uspto-grants-2000_02
Patent number
US06028032

Reaction notes

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