Triethylamine → 4-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 599472Notes

Reaction equation

HRID 599472 reaction equation
Cl.[C:2]([C:6]1[CH:11]=[C:10]([S:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH:9]=[C:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]=1[OH:23])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH2:31]([O:33][C:34]([C:36]1[NH:37][C:38]([CH3:46])=[C:39]([S:42](Cl)(=[O:44])=[O:43])[C:40]=1[CH3:41])=[O:35])[CH3:32]>ClCCl>[CH2:31]([O:33][C:34]([C:36]1[NH:37][C:38]([CH3:46])=[C:39]([S:42]([N:16]2[CH2:17][CH2:18][CH:13]([S:12][C:10]3[CH:9]=[C:8]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:7]([OH:23])=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:11]=3)[CH2:14][CH2:15]2)(=[O:43])=[O:44])[C:40]=1[CH3:41])=[O:35])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2776544ethyl 4-(chlorosulfonyl)-3,5-dimethyl-1H-pyrrole-2-carboxylateHCID 86635427HCID 86635427, compound

Product 1

HCID 866354294-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl esterYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,6-di-tert-butyl-4-(piperidin-4-ylsulfanyl)-phenol hydrochloride (Ex. 3c, 500 mg, 1.4 mmol) in 5 mL of dichloromethane was added triethylamine (495 mg, 4.9 mmol). The mixture was stirred for 3 min followed by the addition of 4-chlorosulfonyl-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (446 mg, 1.68 mmol). The stirring was continued for 3 h at room temperature. The reaction mixture was diluted with Ethyl acetate/hexanes (15 mL, 1:1 v/v), and washed with water (2×20 mL), 0.5 M HCl (2×20 mL) and water (40 mL). It was dried over Na2SO4 and concentrated under reduced pressure to give a brown oil. Chromatography (5-40% Ethyl acetate/hexanes) gave 4-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester as a light-pink foamy solid (620 mg, 80%). ESI/CI-MS m/z 551 ([M+H]+), 549 ([M−H]−).

Workup

  1. waitThe stirring was continued for 3 h at room temperature
  2. washwashed with water (2×20 mL), 0.5 M HCl (2×20 mL) and water (40 mL)
  3. dry with materialIt was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto give a brown oil

Sources & evidence

ORD record
ord-edf379edbfd44d36b84e8511f988823b
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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