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

HRID 1051020Notes

Reaction equation

HRID 1051020 reaction equation
[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C4CCCCO4)[CH:16]=3)(=[O:14])=[O:13])[CH:10]=[C:9]([CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl-].[NH4+]>ClCCl>[C:1]1([C:7]2[N:11]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=3)(=[O:13])=[O:14])[CH:10]=[C:9]([CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 25517Ammonium ChlorideHCID 90168925tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 90168594tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl ((5-(cyclohex-1-en-1-yl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7c (600 mg, 1.1 mmol) was dissolved in 50 mL of dichloromethane, followed by addition of p-toluenesulfonic acid (195 mg, 1.1 mmol), and then the reaction solution was stirred for 3 h. 50 mL of saturated ammonium chloride solution were added, the reaction solution was separated, and the water phase was extracted with dichloromethane (50 mL×3). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system C to obtain the title product tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7d (384 mg, a colorless oil) in 76% yield.

Workup

  1. customthe reaction solution was separated
  2. extractionthe water phase was extracted with dichloromethane (50 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography with elution system C

Sources & evidence

ORD record
ord-1228b9dbd08e48789f104182c7dab2fb
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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