m-Chloroperbenzoic acid → HCID 59625442, compound

HRID 2192822Notes

Reaction equation

HRID 2192822 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][S:15][CH3:16])[C:8]([C:17]([N:19]([CH2:37][CH:38]([CH3:40])[CH3:39])[C@@H:20]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23][C@H:22]([C:33]([O:35][CH3:36])=[O:34])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:49])C=1>ClCCCl.C(=O)([O-])O.[Na+]>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][S:15]([CH3:16])=[O:49])[C:8]([C:17]([N:19]([CH2:37][CH:38]([CH3:40])[CH3:39])[C@@H:20]2[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:23][C@H:22]([C:33]([O:35][CH3:36])=[O:34])[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59625396HCID 59625396, compound

Product 1

HCID 59625442HCID 59625442, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-tert-Butyl 3-methyl (3R,5S)-5-{[(2-tert-butyl-4-{[3-(methylsulfanyl)propyl]amino}pyrimidin-5-yl)carbonyl](2-methylpropyl)amino}piperidine-1,3-dicarboxylate (150 mg) was dissolved in 1,2-dichloroethane (3 ml), 3-chloroperbenzoic acid (65% contained, 70 mg) was added, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane (10:90-85:15) and concentrated under reduced pressure to give the object compound (113 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washeluted with ethyl acetate-hexane (10:90-85:15)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c0f44eaf8334aa18a77506687c1d5e4
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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