Methyl morpholine oxide → HCID 86656356, compound

HRID 1942486Notes

Reaction equation

HRID 1942486 reaction equation
[F:1][CH:2]([F:47])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:22]([N:24]([CH:41]([CH3:43])[CH3:42])[C@H:25]3[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C@@H:28]([CH2:38][CH2:39][OH:40])[CH2:27][CH2:26]3)=[O:23])[C:16]([C:18]([F:21])([F:20])[F:19])=[CH:17][C:12]=2[O:11][C:10]([CH3:45])([CH3:44])[C:9]1=[O:46])=[O:4].C[N+]1([O-])CCOCC1>C(Cl)Cl.C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[F:47][CH:2]([F:1])[C:3]([NH:5][CH2:6][CH2:7][N:8]1[C:13]2[CH:14]=[C:15]([C:22]([N:24]([CH:41]([CH3:42])[CH3:43])[C@H:25]3[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:36])([CH3:37])[CH3:35])=[O:32])[C@@H:28]([CH2:38][CH:39]=[O:40])[CH2:27][CH2:26]3)=[O:23])[C:16]([C:18]([F:20])([F:21])[F:19])=[CH:17][C:12]=2[O:11][C:10]([CH3:45])([CH3:44])[C:9]1=[O:46])=[O:4]

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 67333667HCID 67333667, compound

Product 1

HCID 86656356HCID 86656356, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Under the nitrogen atmosphere, to a solution of tert-butyl (2R,5R)-5-[{[4-{2-[(difluoroacetyl)-amino]ethyl}-2,2-dimethyl-3-oxo-7-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]carbonyl}-(isopropyl)amino]-2-(2-hydroxyethyl)piperidine-1-carboxylate (1.1 g) in methylene chloride -acetonitrile (5 ml, 5 ml) were added N-methylmorpholine oxide (283 mg) and molecular sieve 4 Å (750 mg), and the mixture was stirred at room temperature for a while. Then, tetrapropylammonium perruthenate (56 mg) was added thereto, and the mixture was stirred at room temperature for 3 hours. Then, the insoluble materials were removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (the developing solvent: hexane/acetone=2/1) to give the title compound (757 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. customThen, the insoluble materials were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-b43ed03412e34d74bcc7c5051ad44d20
Source dataset
uspto-grants-2013_03
Patent number
US08389511B2

Reaction notes

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