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

HRID 1051020노트

반응식

HRID 1051020 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1228b9dbd08e48789f104182c7dab2fb
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388133B2

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