Triethylamine → N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine

HRID 1506750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506750
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[CH3:24][S:25]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:16])(=[O:27])=[O:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 3366758Benzyl N-(4-hydroxybutyl)carbamate

Produkt 1

HCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamineAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

To a solution of benzyl 4-hydroxybutylcarbamate (1.1 g, 4.9 mmol) and triethylamine (1.7 mL, 9.8 mmol) in THF was added methanesulfonyl chloride (0.67 g, 5.9 mmol) at 0° C. The reaction was stirred at 20-25° C. for 6 hours and concentrated. The residue was partitioned between ethyl acetate and water. The phases were separated, and the organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline. The separated organic layer was dried and concentrated to give 4-(benzyloxycarbonylamino)butyl methanesulfonate (1.2 g).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe organic layer was washed with hydrochloride solution (1 N), saturated sodium bicarbonate solution, and saline
  5. customThe separated organic layer was dried
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-b20122d48fe34482a3c16ad8d8803456
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09221760B2

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