Triethylamine → HCID 86635425, compound

HRID 599466Notes

Reaction equation

HRID 599466 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([S:17][C:18]2([CH2:24][CH2:25][O:26][C:27](=[O:29])[CH3:28])[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.[CH3:37][O:38][C:39]([C:41]1[N:42]([CH3:50])[C:43]([S:46](Cl)(=[O:48])=[O:47])=[CH:44][CH:45]=1)=[O:40]>ClCCl.C(OCC)(=O)C>[CH3:37][O:38][C:39]([C:41]1[N:42]([CH3:50])[C:43]([S:46]([N:21]2[CH2:20][CH2:19][C:18]([CH2:24][CH2:25][O:26][C:27](=[O:29])[CH3:28])([S:17][C:8]3[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]([OH:12])=[C:6]([C:2]([CH3:3])([CH3:4])[CH3:5])[CH:7]=3)[CH2:23][CH2:22]2)(=[O:48])=[O:47])=[CH:44][CH:45]=1)=[O:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2736899Methyl 5-(chlorosulfonyl)-1-methyl-1H-pyrrole-2-carboxylateHCID 86635423HCID 86635423, compound

Product 1

HCID 86635425HCID 86635425, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To acetic acid 2-[4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidin-4-yl]-ethyl ester hydrochloride (Ex. 1c, 370 mg, 0.83 mmol) in 8 mL of dichloromethane was added triethylamine (293 mg, 2.9 mmol). After stirring for 5 min, 5-chlorosulfonyl-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (296 mg, 1.25 mmol) was added in 3 portions. The reaction mixture was stirred for 3 h at room temperature, and then diluted with Ethyl acetate (40 mL), washed with water (50 mL), 0.5 N HCl (2×30 mL) and water (50 mL), dried over Na2SO4, and concentrated under reduced pressure. The crude product was chromatographed with 5-30% Ethyl acetate/hexanes to afford 5-[4-(2-acetoxy-ethyl)-4-(3,5-di-tert-butyl-4-hydroxy-phenylsulfanyl)-piperidine-1-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester as a clear oil (420 mg, 83%). ESI/CI-MS m/z 609 ([M+H]+).

Workup

  1. stirringThe reaction mixture was stirred for 3 h at room temperature
  2. washwashed with water (50 mL), 0.5 N HCl (2×30 mL) and water (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was chromatographed with 5-30% Ethyl acetate/hexanes

Sources & evidence

ORD record
ord-23e74ba6a8954379890a5009b69037d9
Source dataset
uspto-grants-2011_03
Patent number
US07897776B2

Reaction notes

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