m-Chloroperbenzoic acid → HCID 86670938, compound

HRID 515282Notes

Reaction equation

HRID 515282 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]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH:31]4[CH2:35][CH2:34][S: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>[F:5][C:4]([F:7])([F:6])[C:3]([C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][CH:31]4[CH2:35][CH2:34][S:33](=[O:45])[CH2:32]4)=[O:29])=[CH:23][CH:22]=3)[CH2:16][CH2:15]2)=[CH:36][CH:37]=1)([OH:8])[C:2]([F:38])([F:1])[F:39]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 86670939HCID 86670939, compound

Product 1

HCID 86670938HCID 86670938, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 1-(4-((1-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)methyl)phenyl)-3-(tetrahydrothiophen-3-yl)urea (0.243 mmol, 140 mg) in dichloromethane was added 3-chloroperoxybenzoic acid (0.243 mmol, 54.5 mg) and the resulting mixture was stirred for 30 minutes. Additional 3-chloroperoxybenzoic acid (0.243 mmol, 54.5 mg) was added and reaction stirred for 1.5 hours. The reaction was concentrated under vacuum. The residue was purified by silica column chromatography (eluent: 2% methanol in dichloromethane-7% methanol in dichloromethane) and SCX chromatography to give the title compound (77.1 mg).

Workup

  1. customreaction
  2. stirringstirred for 1.5 hours
  3. concentrationThe reaction was concentrated under vacuum
  4. customThe residue was purified by silica column chromatography (eluent: 2% methanol in dichloromethane-7% methanol in dichloromethane) and SCX chromatography

Sources & evidence

ORD record
ord-04eb360ff2894ed688b32ce41f78938b
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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