Undec-4-ene → HCID 54373433, compound

HRID 1756789Notes

Reaction equation

[NH2:1][C:2]1[C:3]([N:10]([CH3:12])[CH3:11])=[N:4][CH:5]=[N:6][C:7]=1[O:8][CH3:9].C([O:15][C:16]([NH:18][CH2:19][C@@H:20]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]2[O:32][CH2:33][O:34][C:27]=12)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=O)C.[CH3:35]CCCCCC=CCCC>O1CCOCC1>[CH2:33]1[O:32][C:28]2[C:27](=[C:26]([C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:19][NH:18][C:16]([NH:1][C:2]3[C:3]([N:10]([CH3:11])[CH3:12])=[N:4][CH:5]=[N:6][C:7]=3[O:8][CH2:9][CH3:35])=[O:15])[CH:31]=[CH:30][CH:29]=2)[O:34]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 0.66 g of 5-amino-4-dimethylamino-6-methoxypyrimidine, 1.28 g of N-ethoxycarbonyl-(R)-2-(2, 3-methylenedioxyphenyl) heptylamine, 0.55 g of 1, 8-diazabicyclo [5, 4, 0] undec-7-ene and 10 ml of dioxane was stirred at 100° C. for 16 hours and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate-n-hexane (2:1-3:1), and the product was dissolved in ether. The solution was washed with water and saturated saline in this order, dried over anhydrous sodium sulfate and the solvent evaporated. The residue was triturated with n-hexane to give 0.63 g of the titled compound.

Workup

customthe solvent evaporated
customThe residue was chromatographed on a silica gel column
washeluting with ethyl acetate-n-hexane (2:1-3:1)
dissolutionthe product was dissolved in ether
washThe solution was washed with water and saturated saline in this order
dry with materialdried over anhydrous sodium sulfate
customthe solvent evaporated
customThe residue was triturated with n-hexane

Sources & evidence

ORD record: ord-e41dc2650e004e7ca4d7022b86c1fc4b
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05442060

Reaction notes

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