Ethanolamine → Benzoic acid, 3-(6-amino-3-methyl-2-pyridinyl)-, 1,1-dimethylethyl ester

HRID 242135

Reaktionsgleichung

Reaktionsgleichung von HRID 242135
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N+:15]=2[O-])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:22]1C=CC=CC=1.CS(OS(C)(=O)=O)(=O)=O.C(CN)O>CC#N.O>[C:1]([O:5][C:6](=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]2[C:19]([CH3:20])=[CH:18][CH:17]=[C:16]([NH2:22])[N:15]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 700EthanolamineHCID 1049PyridineHCID 81560Methanesulfonic anhydrideHCID 584883712-(3-(Tert-butoxycarbonyl)phenyl)-3-methylpyridine 1-oxide

Produkt 1

HCID 45480517Benzoic acid, 3-(6-amino-3-methyl-2-pyridinyl)-, 1,1-dimethylethyl esterAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A solution of 2-(3-(tert-butoxycarbonyl)phenyl)-3-methylpyridine-1-oxide (1 eq) and pyridine (4 eq) in MeCN (8 vol.) is heated to 70° C. A solution of methanesulfonic anhydride (1.5 eq) in MeCN (2 vol) is added over 50 min via addition funnel maintaining the temperature at less than 75° C. The mixture is stirred for an additional 0.5 hours after complete addition. The mixture is then allowed to cool to ambient. Ethanolamine (10 eq) is added via addition funnel. After stirring for 2 hours, water (6 vol.) is added and the mixture is cooled to 10° C. After stirring for NLT 3 hours, the solid is collected by filtration and washed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol). The solid is dried to constant weight (<1% difference) in a vacuum oven at 50° C. with a slight N2 bleed to afford tert-butyl-3-(6-amino-3-methylpyridin-2-yl)benzoate as a red-yellow solid (53% yield).

Aufarbeitung

  1. temperaturemaintaining the temperature at less than 75° C
  2. additionafter complete addition
  3. temperatureto cool to ambient
  4. stirringAfter stirring for 2 hours
  5. stirringAfter stirring for NLT 3 hours
  6. filtrationthe solid is collected by filtration
  7. washwashed with water (3 vat), 2:1 MeCN/water (3 vol), and MeCN (2×1.5 vol)
  8. dry with materialThe solid is dried to constant weight (<1% difference) in a vacuum oven at 50° C. with a slight N2

Quellen und Nachweise

ORD-Eintrag
ord-7ca89493c8724daca4f6cf6f6b38bb6d
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653103B2

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