p-Toluenesulfonic acid → tert-butyl ((5-(2-fluorophenyl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051002Notes

Reaction equation

HRID 1051002 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C3CCCCO3)[CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH:9]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:29][N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:34])([CH3:35])[CH3:36])[CH:9]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 90168696tert-butyl ((5-(2-fluorophenyl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 90168587tert-butyl ((5-(2-fluorophenyl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl ((5-(2-fluorophenyl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 1g (0.45 g, 0.83 mmol) was dissolved in 5 mL of methanol, followed by addition of p-toluenesulfonic acid (16 mg, 0.08 mmol), and then the reaction solution was stirred for 3 h. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography with elution system B to obtain the title product tert-butyl ((5-(2-fluorophenyl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 1h (0.35 g, a red oil) in 92% yield.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography with elution system B

Sources & evidence

ORD record
ord-e78e6e7500304a8fa3a06982b4680796
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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