m-Chloroperbenzoic acid → (5R)-5-(3,5-difluorophenyl)-2,2-dimethylthiomorpholin-3-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14](CC(NC3C=C4C(=CC=3)C[C@@]3(C(=O)NC(=O)N3C)C4)=O)[C:13](=[O:35])[C:12]([CH3:37])([CH3:36])[S:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[F:8][C:6]1[CH:5]=[C:4]([C@H:9]2[NH:14][C:13](=[O:35])[C:12]([CH3:37])([CH3:36])[S:11][CH2:10]2)[CH:3]=[C:2]([F:1])[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-[(5R)-5-(3,5-difluorophenyl)-2,2-dimethyl-3-oxo-4-thiomorpholinyl]-N-[(4S)-3-methyl-2,5-dioxo-1′,3′-dihydrospiro[imidazolidine-4,2′-inden]-5′-yl]acetamide (Example 2) in 1.5 mL chloroform at 0° C., was added 3-chloroperoxybenzoic acid (21 mg with a purity of 77%, 0.121 mmol). An LCMS of the reaction mixture after two hours showed that all starting material was consumed. Calcium hydroxide (14 mg, 0.185 mmol) was added to the reaction and stirred for forty minutes. The mixture was then vacuum filtered through filter paper and the solid was washed with chloroform (3×10 mL). The filtrate was concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of MeOH:CH2Cl2—1:99 to 5:95, to give the title compound. MS: m/z=545 (M+H). HRMS: m/z 545.1653; calculated m/z=545.1665 for C26H26F2N4O5S.
Workup
- customwas consumed
- filtrationvacuum filtered
- filtrationthrough filter paper
- washthe solid was washed with chloroform (3×10 mL)
- concentrationThe filtrate was concentrated in vacuo
- customto give a residue that
- customwas purified by silica gel chromatography
- washeluting with a gradient of MeOH
Sources & evidence
- ORD record
- ord-8a2950f876424925b59dcfa2e4d8e516
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629338B2
Reaction notes
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