Triethylamine → (6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonate

HRID 1189752Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189752
[CH3:1][S:2]([O:5]S(C)(=O)=O)(=[O:4])=[O:3].[C:10]([O:14][C:15](=[O:25])[NH:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][N:18]=1)([CH3:13])([CH3:12])[CH3:11].C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O.O>[C:10]([O:14][C:15]([NH:16][C:17]1[N:18]=[CH:19][C:20]([CH2:23][O:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:21][CH:22]=1)=[O:25])([CH3:13])([CH3:12])[CH3:11]

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 81560Methanesulfonic anhydrideHCID 3575389tert-Butyl 5-(hydroxymethyl)pyridin-2-ylcarbamate

Produkt 1

HCID 86641141(6-(Tert-butoxycarbonylamino)pyridin-3-yl)methyl methanesulfonateAusbeute 91,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Methanesulfonic anhydride (0.854 g, 4.9 mmol, 1.1 equiv) was added portionwise to a cold (5° C.) mixture of (5-hydroxymethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (Step 26.4) (1 g, 4.5 mmol) and triethylamine (0.75 mL, 5.4 mmol, 1.2 equiv) in DCM (20 mL), under an argon atmosphere. The reaction mixture was allowed to stir for 1 h at 5° C., diluted with EtOAc and H2O, and extracted with EtOAc. The organic phase was washed with H2O and brine, dried (Na2SO4), filtered and concentrated to provide 1.25 g of the title compound as a white solid: tR=2.60 min (System 1).

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e6a0ab89adab4233a24a77757ffac281
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674099B2

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