Sodium Hydroxide → HCID 69354532, compound

HRID 1271300Notes

Reaction equation

HRID 1271300 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13][C:14]1[CH:19]=[N:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)([CH3:4])([CH3:3])[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:38].[OH-].[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:32])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][S:13]([C:14]1[CH:19]=[N:18][C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:15]=1)=[O:38])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 69354035HCID 69354035, compound

Product 1

HCID 69354532HCID 69354532, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

While stirring under ice cooling, to a solution of 350 mg of 2-{4-[(5,6-diphenylpyrazin-2-yl)thio]butyloxy}acetic acid tert-butyl ester obtained in Example 34 in 5 ml of chloroform, 191 mg of 70% m-chloroperoxybenzoic acid was added, followed by stirring for 2 hours. The reaction solution was combined with 20 ml of a 0.2N sodium hydroxide solution, extracted with chloroform and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 145 mg of the desired compound as a pale yellow oily substance.

Workup

  1. additionwas added
  2. extractionextracted with chloroform
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b3a4bf068a5d4bf0b1a966eebe9e0157
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

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