Hydrochloric Acid → Ethyl 3-chloro-6-(pivalamidomethyl)picolinate

HRID 1469713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1469713
C(O[C:6]([NH:8][CH2:9][C:10]1[N:15]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:13]([Cl:21])=[CH:12][CH:11]=1)=[O:7])(C)(C)C.Cl.[C:23](Cl)(=O)[C:24](C)([CH3:26])[CH3:25]>CCOC(C)=O>[Cl:21][C:13]1[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[C:24]([CH3:26])([CH3:25])[CH3:23])=[CH:11][CH:12]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 86692224Ethyl 6-(((tert-butoxycarbonyl)amino)methyl)-3-chloropicolinate

Produkt 1

HCID 86692225Ethyl 3-chloro-6-(pivalamidomethyl)picolinateAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

A solution of ethyl 6-(((tert-butoxycarbonyl)amino)methyl)-3-chloropicolinate (100 mg, 0.318 mmol) in EtOAc saturated with HCl (1 mL) was stirred at rt for 1 h. The reaction mixture was concentrated and the concentrate was dissolved in CH2Cl2 (2 mL). The solution was treated with DIPEA (0.5 mL) followed by pivaloyl chloride (38 mg, 0.318 mmol) at 0° C. The reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc and was washed with H2O and brine. The organic layer was separated, dried, filtered and concentrated to afford 85 mg of the title product. 1H NMR (300 MHz, DMSO-d6): δ 8.26 (br t, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.35 (d, J=8.1 Hz, 1H), 4.40-4.31 (m, 4H), 1.33-1.10 (m, 12H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe concentrate was dissolved in CH2Cl2 (2 mL)
  3. additionThe solution was treated with DIPEA (0.5 mL)
  4. washwas washed with H2O and brine
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0cae618dd96d423381c2b09bec0f53c4
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006257B2

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