m-Chloroperbenzoic acid → 1-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylsulfinyl)phenyl)-3-((S)-tetrahydrofuran-3-yl)urea

HRID 515320Notes

Reaction equation

HRID 515320 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]([C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([S:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C@H:31]4[CH2:35][CH2:34][O:33][CH2:32]4)=[O:29])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].ClC1C=C(C=CC=1)C(OO)=[O:45]>ClCCl.CO>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:37]=[CH:36][C:12]([CH2:13][N:14]2[CH2:15][CH2:16][CH:17]([S:20]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C@H:31]4[CH2:35][CH2:34][O:33][CH2:32]4)=[O:29])=[CH:23][CH:22]=3)=[O:45])[CH2:18][CH2:19]2)=[CH:11][CH:10]=1)([OH:8])[C:2]([F:38])([F:1])[F:39]

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86670956HCID 86670956, compound

Product 1

HCID 866709571-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylsulfinyl)phenyl)-3-((S)-tetrahydrofuran-3-yl)urea

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(S)-1-(4-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-ylthio)phenyl)-3-(tetrahydrofuran-3-yl)urea (0.246 mmol, 142 mg) was dissolved in dichloromethane (5 mL) and the solution cooled to 0° C. 3-Chlorobenzoperoxoic acid (0.246 mmol, 42.4 mg) was added and the reaction mixture stirred for 2 hours. The reaction mixture was diluted with methanol and dichloromethane. The reaction mixture was washed with water and the organic layer separated, dried, and concentrated under vacuum. The residue was purified by silica column chromatography (eluting with a dichloromethane/methanol/ammonia gradient) to afford the title compound. MS m/z 594.5 [M+H]+

Workup

  1. washThe reaction mixture was washed with water
  2. customthe organic layer separated
  3. customdried
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica column chromatography (
  6. washeluting with a dichloromethane/methanol/ammonia gradient)

Sources & evidence

ORD record
ord-3b4ad3ff30a142db84920115a4639a3d
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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