m-Chloroperbenzoic acid → HCID 59627214, compound

HRID 1523260Notes

Reaction equation

HRID 1523260 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]([CH3:25])=[CH2:24])([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:35])C=1>C(Cl)Cl.C(OC)(C)(C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@:13]([CH2:22][C:23]3([CH3:25])[CH2:24][O:35]3)([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:12][C:11]2=[O:26])[CH3:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59627202HCID 59627202, compound

Product 1

HCID 59627214HCID 59627214, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of (R)-1-((5)-1-(4-bromophenyl)ethyl)-4-(2-methylallyl)-4-phenyltetrahydropyrimidin-2(1H)-one (0.6 g, 1.45 mmol) in CH2Cl2 (15 mL) was added to m-CPBA (0.59 g, 2.9 mmol). The resulting solution was stirred overnight. The mixture was diluted with methyl tert-butyl ether (100 mL) and washed with 30 wt % aq sodium thiosulfate (3×50 mL) and saturated aqueous sodium bicarbonate (3×50 mL). The organic layer was dried over Na2SO4, filtered and then concentrated to afford (4S)-1-((S)-1-(4-bromophenyl)ethyl)-4-((2-methyloxiran-2-yl)methyl)-4-phenyltetrahydropyrimidin-2(1H)-one (0.61 g, Yield: 98%).

Workup

  1. washwashed with 30 wt % aq sodium thiosulfate (3×50 mL) and saturated aqueous sodium bicarbonate (3×50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ea81e2a13e9d457097212a94a7db0168
Source dataset
uspto-grants-2015_07
Patent number
US09079861B2

Reaction notes

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