N-(tert-Butoxycarbonyl)-1,5-diaminopentane → Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate

HRID 1408313Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408313
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25])([O-:17])=[O:16].C(N(C(C)C)CC)(C)C>C(Cl)Cl.C(OC(C)C)(C)C>[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])(=[O:26])=[O:25])([O-:17])=[O:16]

Komponenten

6

Edukt 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531Diisopropylethylamine

Produkt 1

HCID 67226448Tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7914Diisopropyl EtherLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 5-aminopentylcarbamate 30a (20 g, 99 mmoles) and 2-nitrobenzene-1-sulfonyl chloride 30b (23 g, 1.05 eq) in DCM (200 mL) was added dropwise diisopropyl ethyl amine (19.2 g, 1.5 eq) at 0° C. After stirring at RT overnight, the RM was successively washed with an aqueous solution of citric acid, then brine, dried over magnesium sulfate, filtered and concentrated. Trituration in diisopropyl ether afforded 32.61 g (85% yield) of tert-butyl 5-(2-nitrophenylsulfonamido)pentylcarbamate 30c as a white solid; m/z 388 [M+H]+.

Aufarbeitung

  1. washthe RM was successively washed with an aqueous solution of citric acid
  2. dry with materialbrine, dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f1860e48b584f17b7d850c8d8f6f019
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921355B2

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