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Sodium Carbonate → HCID 44517832, compound

HRID 1951122
Notes
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Reaction equation

HRID 1951122 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23]SC)[CH2:17][CH2:16]3)=[O:14])[CH2:10][CH:9]2[N:26]([CH3:41])[C:27](=[O:40])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([C:36]([F:39])([F:38])[F:37])[CH:29]=2)=[CH:4][CH:3]=1.Cl[C:43]1C=CC=C(C(OO)=O)C=1.[S:53](=[O:57])(=O)(O)[O-:54].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][N:11]([C:13]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][S:53]([CH3:43])(=[O:57])=[O:54])[CH2:19][CH2:20]3)=[O:14])[CH2:10][CH:9]2[N:26]([CH3:41])[C:27](=[O:40])[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([C:36]([F:37])([F:39])[F:38])[CH:29]=2)=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516919Sodium BisulfateHCID 67025603HCID 67025603, compound

Product 1

HCID 44517832HCID 44517832, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-{(3RS,4SR)-4-(4-chloro-phenyl)-1-[1-(3-methylsulfanyl-propyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-4-methoxy-N-methyl-3-trifluoromethyl-benzamide (80 mg, 0.13 mmol) in dichloromethane (2 mL) was added under an atmosphere of nitrogen m-chloroperbenzoic acid (47 mg, 0.27 mmol) and stirred for 3 d at ambient temperature. Further addition of m-chloroperbenzoic acid (47 mg, 0.27 mmol) was followed by stirring for 3 h at ambient temperature. After the addition of an aqueous saturated solution of sodium bisulfate (10 mL) and water (10 mL) it was stirred for 1 h at ambient temperature. The reaction mixture was basified by addition of an aqueous solution of sodium carbonate (1 M). The aqueous layer was extracted with dichloromethane (20 mL) and the organic layers were washed with water (15 mL) and dried over sodium sulfate. Purification by chromatography (SiO2, heptane:(ethyl acetate:triethylamine=95:5):methanol=20:80:0 to 0:85:15) afforded the title compound (70 mg, 83%) as a light brown oil. MS m/e: 644.2 [M]+.

Workup

  1. stirringby stirring for 3 h at ambient temperature
  2. stirringwas stirred for 1 h at ambient temperature
  3. extractionThe aqueous layer was extracted with dichloromethane (20 mL)
  4. washthe organic layers were washed with water (15 mL)
  5. dry with materialdried over sodium sulfate
  6. customPurification by chromatography (SiO2, heptane:(ethyl acetate:triethylamine=95:5):methanol=20:80:0 to 0:85:15)

Sources & evidence

ORD record
ord-5ef31a8228e74b8485b2fbde7fa65ca5
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08404679B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes