Triethylamine → (R)-2-t-butoxycarbonylamino-1-hexyl methanesulfonate

HRID 977529Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 977529
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([O:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:12][CH2:13][CH2:14][CH3:15])(=[O:26])=[O:25]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53987300HCID 53987300, Verbindung

Produkt 1

HCID 54485960(R)-2-t-butoxycarbonylamino-1-hexyl methanesulfonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-t-butoxycarbonylamino-1-hexanol (2.17 g, prepared in (1)) in dichloromethane (20 ml) were added triethylamine (1.67 ml) and methanesulfonyl chloride (0.93 ml) under ice cooling. After being stirred at the same temperature for 1 h, the mixture was washed with water, 10% aq. citric acid, sat. aq NaHCO3 and brine successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=2/1 for elution to give the product (1.32 g).

Aufarbeitung

  1. washthe mixture was washed with water, 10% aq. citric acid, sat. aq NaHCO3 and brine successively
  2. dry with materialdried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by silica gel chromatography (Merck, Kieselgel 60) with hexane/ethyl acetate=2/1 for elution

Quellen und Nachweise

ORD-Eintrag
ord-a9432794bab949dc8de1e5f4986cb7f5
Quelldatensatz
uspto-grants-1997_03
Patentnummer
US05614498

Notizen zur Reaktion

Wird geladen…