Water → HCID 66817566, compound

HRID 1755048Notes

Reaction equation

HRID 1755048 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].COC1N=C(OC)N=C([O:17][C:18](=O)[C:19]2[CH:24]=[C:23]([CH3:25])[C:22](/[CH:26]=[CH:27]/[S:28]([N:31]3[CH2:47][CH2:46][C:34]4([N:38]=[C:37]([CH:39]5[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]5)[NH:36][C:35]4=[O:45])[CH2:33][CH2:32]3)(=[O:30])=[O:29])=[C:21]([CH3:48])[CH:20]=2)N=1.C(N(CC)CC)C.O>C(#N)C>[CH:39]1([C:37]2[NH:36][C:35](=[O:45])[C:34]3([CH2:33][CH2:32][N:31]([S:28](/[CH:27]=[CH:26]/[C:22]4[C:23]([CH3:25])=[CH:24][C:19]([C:18]([N:3]5[CH2:4][CH2:5][O:1][C:2]5=[O:6])=[O:17])=[CH:20][C:21]=4[CH3:48])(=[O:30])=[O:29])[CH2:47][CH2:46]3)[N:38]=2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 739492-OxazolidinoneHCID 66816522HCID 66816522, compound

Product 1

HCID 66817566HCID 66817566, compoundYield 33.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Oxazolidin-2-one (47 mg, 0.53 mmol) was added to a solution of 4-[(E)-2-(2-cyclohexyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-vinyl]-3,5-dimethyl-benzoic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester (109 mg, 0.17 mmol) and triethylamine (0.12 ml, 0.88 mmol) in anhydrous acetonitrile (1 ml), and the mixture was heated with stirring at 80° C. for 15 hours. The mixture was cooled and water was then added, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-methanol) to give 2-cyclohexyl-8-{(E)-2-[2,6-dimethyl-4-(2-oxo-oxazolidine-3-carbonyl)-phenyl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (31 mg, 32%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-methanol)

Sources & evidence

ORD record
ord-9d75a54f5e7049d69a0c26addd56812c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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