Triphenylphosphine → tert-butyl ((5-(2-fluorophenyl)-1-((4-((1-(methylcarbamoyl)cyclopropyl)methoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051017Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1051017
[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][C:19]([OH:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:11]=[C:10]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH:9]=1.O[CH2:34][C:35]1([C:38]([NH:40][CH3:41])=[O:39])[CH2:37][CH2:36]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[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:17]=[CH:18][C:19]([O:22][CH2:34][C:35]3([C:38](=[O:39])[NH:40][CH3:41])[CH2:37][CH2:36]3)=[CH:20][CH:21]=2)(=[O:14])=[O:15])[CH:11]=[C:10]([CH2:23][N:24]([CH3:32])[C:25](=[O:31])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])[CH:9]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 90168684tert-butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamateHCID 901686851-(Hydroxymethyl)-N-methylcyclopropanecarboxamide

Produkt 1

HCID 90168686tert-butyl ((5-(2-fluorophenyl)-1-((4-((1-(methylcarbamoyl)cyclopropyl)methoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

tert-Butyl ((5-(2-fluorophenyl)-1-((4-hydroxyphenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 4d (100 mg, 0.22 mmol), 1-(hydroxymethyl)-N-methyl cyclopropanecarboxamide 5c (47 mg, 0.33 mmol), diisopropyl azodicarboxylate (150 mg, 0.65 mmol) and triphenylphosphine (171 mg, 0.65 mmol) were added to 3 mL of dichloromethane and then the reaction solution was stirred for 16 h. The reaction solution was concentrated under reduced pressure, and the resulting residue was purified by thin layer chromatography with elution system B to obtain the title product tert-butyl ((5-(2-fluorophenyl)-1-((4-((1-(methylcarbamoyl)cyclopropyl)methoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 6a (100 mg, a yellow oil) in 81% yield.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-8df7497df9d14bb2b823d05ed3dbbd3f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09388133B2

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