Hydrogen Bromide → HCID 22118296, compound

HRID 1274878Notes

Reaction equation

HRID 1274878 reaction equation
[BrH:1].[CH3:2][C:3]1[O:8][CH2:7][N:6]([C:9]([CH3:17])([C:11](=[O:16])[CH2:12][CH2:13][CH:14]=[CH2:15])[CH3:10])[C:5](=[O:18])[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)(=O)C>[Br:1][CH:14]([CH3:15])[CH2:13][CH2:12][C:11](=[O:16])[C:9]([N:6]1[C:5](=[O:18])[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:3]([CH3:2])[O:8][CH2:7]1)([CH3:10])[CH3:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22118272HCID 22118272, compound

Product 1

HCID 22118296HCID 22118296, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Hydrogen bromide solution in acetic acid (50 g of 30% w/w) was added to 2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-hept-6-en-3-one (4.14 g) and stirred for 5 hours. Evaporation and dry column chromatography on silica gel eluting with hexane/ethyl acetate (4:1) gave 6-bromo-2-(2,3-dihydro-6-methyl-4-oxo-5-phenyl-4H-1,3-oxazin-3-yl)-2-methyl-heptan-3-one (1.04 g) as a brown gum, NMR 1.4(s,6H), 1.7(d,3H), l.9(m,1H), 1.9(s,3H), 2.2(m,1H), 2.7(m,2H), 4.1(m,1H), 5.3(s,2H), 7.3(m,5H).

Workup

  1. customEvaporation
  2. dry with materialdry column chromatography on silica gel eluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-c2663371f14c4d28a7b51bb0e51ea1b7
Source dataset
uspto-grants-2000_12
Patent number
US06159902

Reaction notes

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