m-Chloroperbenzoic acid → HCID 86635431, compound

HRID 599477Notes

Reaction equation

HRID 599477 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:35])[C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([S:19][C:20]3[CH:25]=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=3)[CH2:15][CH2:14]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1)=[O:4].ClC1C=CC=C(C(OO)=[O:44])C=1>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:35])[C:7]([S:10]([N:13]2[CH2:18][CH2:17][CH:16]([S:19]([C:20]3[CH:25]=[C:24]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:23]([OH:30])=[C:22]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH:21]=3)=[O:44])[CH2:15][CH2:14]2)(=[O:11])=[O:12])=[CH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866354305-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester

Product 1

HCID 86635431HCID 86635431, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (Ex. 4a, 490 mg, 0.94 mmol) in 10 mL of dichloromethane at room temperature under N2 was added m-chloroperbenzoic acid (247 mg, 1.1 mmol) in 5 portions during a period of 30 min. The resulting suspension was stirred for 3 h at room temperature and then the reaction was quenched by pouring the suspension onto ice (20 g). The mixture was extracted with ethyl acetate (2×40 mL) and the combined organic phase was dried over Na2SO4 and concentrated under reduced pressure. Chromatography (3-50% Ethyl acetate/hexanes) gave 5-[4-(3,5-di-tert-butyl-4-hydroxy-benzenesulfinyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester a white solid (480 mg, 95%). ESI/Cl-MS m/z 537 ([M−H]−).

Workup

  1. customthe reaction was quenched
  2. additionby pouring the suspension onto ice (20 g)
  3. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
  4. dry with materialthe combined organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a268dd1af15947c2861820e64c473f95
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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