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Hydrochloric Acid → 4-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid

HRID 2189984
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2189984
C([O:3][C:4]([C:6]1([CH2:27][CH:28]2[CH2:30][CH2:29]2)[CH2:11][CH2:10][N:9]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[O:13])[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C>[CH:28]1([CH2:27][C:6]2([C:4]([OH:5])=[O:3])[CH2:11][CH2:10][N:9]([C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)=[CH:16][CH:15]=3)=[O:13])[CH2:8][CH2:7]2)[CH2:30][CH2:29]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595279394-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 595277804-Cyclopropylmethyl-1-(4'-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702Ethanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A mixture of 0.51 g (1.24 mmol) 4-cyclopropylmethyl-1-(4′-fluoro-biphenyl-4-carbonyl)-piperidine-4-carboxylic acid ethyl ester and 1.87 mL 4N NaOH aq. in 5 mL ethanol was stirred at 75° C. for a prolonged period of time. After concentration of the mixture ice-water was added and the pH was adjusted to pH=2 with HCl aq. The mixture was extracted with ethyl acetate, the combined organic layers were dried with Na2SO4, filtered, evaporated to dryness and purified by column chromatography on silica eluting with a gradient formed from ethyl acetate, heptane and formic acid to yield after evaporation of the product containing fractions 0.146 g (31%) of the title compound as white foam. MS ISP (m/e): 382.3 [(M+H)+].

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried with Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. custompurified by column chromatography on silica eluting with a gradient
  6. customformed from ethyl acetate, heptane and formic acid
  7. customto yield
  8. customafter evaporation of the product
  9. additioncontaining fractions 0.146 g (31%) of the title compound as white foam

Quellen und Nachweise

ORD-Eintrag
ord-201eb397257040f89199e4e3c2ea58f2
Quelldatensatz
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08324250B2

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