Methyl morpholine oxide → HCID 86672793, compound

HRID 1755090Notes

Reaction equation

HRID 1755090 reaction equation
C[N+]1([O-])CCOCC1.[OH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[NH:23][C:22](=[O:24])[C:21]2([CH2:29][CH2:28][N:27]([S:30]([CH2:33][CH2:34][C:35]3[C:40]([CH3:41])=[CH:39][C:38]([N:42]([CH3:46])[C:43]([NH2:45])=[O:44])=[CH:37][C:36]=3[CH3:47])(=[O:32])=[O:31])[CH2:26][CH2:25]2)[N:20]=1>C(Cl)Cl.CCC[N+](CCC)(CCC)CCC.[O-][Ru](=O)(=O)=O>[CH3:41][C:40]1[CH:39]=[C:38]([N:42]([CH3:46])[C:43]([NH2:45])=[O:44])[CH:37]=[C:36]([CH3:47])[C:35]=1/[CH:34]=[CH:33]/[S:30]([N:27]1[CH2:28][CH2:29][C:21]2([N:20]=[C:19]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]=[O:9])[NH:23][C:22]2=[O:24])[CH2:25][CH2:26]1)(=[O:31])=[O:32]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 66817472HCID 66817472, compound

Product 1

HCID 86672793HCID 86672793, compoundYield 71.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

NMO (22.0 mg, 0.192 mmol), Molecular Sieves 4A (25.0 mg) and TPAP (0.700 mg, 0.00213 mmol) were added to a solution of 1-(4-{2-[2-(9-hydroxy-nonyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3,5-dimethyl-phenyl)-1-methyl-urea (24.0 mg, 0.0426 mmol) in CH2Cl2 (850 μl) at room temperature. The mixture was stirred at room temperature for one hour and then filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 1-(3,5-dimethyl-4-{(E)-2-[4-oxo-2-(9-oxo-nonyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-1-methyl-urea (17.0 mg, 71%).

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-17434fdee6c74413ac9e619b979308bb
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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