N-(tert-Butoxycarbonyl)-1,5-diaminopentane → Tert-butyl (5-((2-chloroethyl)sulfonamido)pentyl)carbamate

HRID 885494

Reaktionsgleichung

Reaktionsgleichung von HRID 885494
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][S:25]([CH2:24][CH2:23][Cl:22])(=[O:27])=[O:26])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 4352N-(tert-Butoxycarbonyl)-1,5-diaminopentaneHCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-

Produkt 1

HCID 86594118Tert-butyl (5-((2-chloroethyl)sulfonamido)pentyl)carbamateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(tert-butoxycarbonylamino)pentylamine (1.00 g, 4.94 mmol) and triethylamine (689 μL g, 4.94 mmol) in dichloromethane (22 mL) at 0° C. was added 2-chloro-1-ethanesulfonyl chloride (470 μL, 4.50 mmol). The reaction mixture was stirred for 2 h at room temperature and then washed with saturated aqueous sodium bicarbonate solution (15 mL). The organic layer was dried (Na2SO4) and the solvent was removed under reduced pressure to give the title compound (100% yield), which was used in the next step without further purification.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate solution (15 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f94f1ff505394c20ae8c0967476c6257
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08242135B2

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