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Triethylamine → N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-propylenediamine

HRID 10490
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 10490
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH:20]1[C:29]2[CH:28]=[CH:27][CH:26]=[C:25]([S:30](Cl)(=[O:32])=[O:31])[C:24]=2[CH:23]=[CH:22][N:21]=1>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:30]([C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[CH:23]=[CH:22][N:21]=[CH:20]2)(=[O:31])=[O:32])=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 33716555-Isoquinolinesulfonyl chloride

Produkt 1

HCID 21979958N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-propylenediamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of N-(tert-butoxycarbonyl)-1,3-propylenediamine (2.09 g, Tokyo Kasei Kogyo) and triethylamine (3.4 ml, Tokyo Kasei Kogyo) in dichloromethane (20 ml) was added with a solution of isoquinoline-5-sulfonyl chloride (2.73 g, prepared according to Japanese Patent Unexamined Publication (Kokai) No. 61-227581) in dichloromethane (15 ml) with stirring and ice cooling and stirred at room temperature for 14 hours and 30 minutes. The reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine. The organic layer was dried, and then the solvent was evaporated under reduced pressure. Then, the residue was purified by flash column chromatography (chloroform:methanol=50:1) to obtain the title compound (4 g).

Aufarbeitung

  1. customprepared
  2. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  3. customThe organic layer was dried
  4. customthe solvent was evaporated under reduced pressure
  5. customThen, the residue was purified by flash column chromatography (chloroform:methanol=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-e7e86c6093174ea1bac2f28462d3f752
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07094789B2

Notizen zur Reaktion

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