Triethylamine → 5-[4-(3,5-Di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-furan-2-carboxylic acid methyl ester

HRID 599480Notes

Reaction equation

HRID 599480 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.[CH3:31][O:32][C:33]([C:35]1[O:36][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:38][CH:39]=1)=[O:34]>ClCCl>[CH3:31][O:32][C:33]([C:35]1[O:36][C:37]([S:40]([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:42])=[O:41])=[CH:38][CH:39]=1)=[O:34]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2736845Methyl 5-(Chlorosulfonyl)-2-FuroateHCID 86635427HCID 86635427, compound

Product 1

HCID 866354335-[4-(3,5-Di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-furan-2-carboxylic acid methyl esterYield 74.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,6-di-tert-butyl-4-(piperidin-4-ylsulfanyl)-phenol hydrochloride (Ex. 3c, 280 mg, 0.78 mmol) in 5 mL of dichloromethane was added triethylamine (240 mg, 2.37 mmol). The mixture was stirred for 3 min followed by the addition of 5-chlorosulfonyl-furan-2-carboxylic acid methyl ester (210 mg, 0.94 mmol). The stirring was continued for 2 h at room temperature and then the reaction was quenched with 20 mL of saturated NaH2PO4. The mixture was extracted with Ethyl acetate (40 mL) and the 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-phenylsulfanyl)-piperidine-1-sulfonyl]-furan-2-carboxylic acid methyl ester as a clear oil (295 mg, 74%). ESI/CI-MS m/z 508 ([M−H]−).

Workup

  1. waitThe stirring was continued for 2 h at room temperature
  2. customthe reaction was quenched with 20 mL of saturated NaH2PO4
  3. extractionThe mixture was extracted with Ethyl acetate (40 mL)
  4. dry with materialthe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-77fe4c6fb40a48fdb3f88474610503a3
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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