m-Chloroperbenzoic acid → HCID 69057118, compound

HRID 1864919Notes

Reaction equation

HRID 1864919 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]([CH: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]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 250207092-[(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

Product 1

HCID 69057118HCID 69057118, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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 fourty 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

  1. customwas consumed
  2. filtrationvacuum filtered
  3. filtrationthrough filter paper
  4. washthe solid was washed with chloroform (3×10 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue that
  7. customwas purified by silica gel chromatography
  8. washeluting with a gradient of MeOH

Sources & evidence

ORD record
ord-bcaf9ed650a04c498653dd2022454430
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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