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Triethylamine → 4-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl Ester

HRID 1831316
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1831316
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]([OH:15])=[CH:13][CH:14]=2)=[O:7])=[CH:4][CH:3]=1.C(NC1C=CC([O:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([O:42][Si](C(C)(C)C)(C)C)[CH2:38][CH2:37]2)=O)=NC=1)(=O)C1C=CC=CC=1.C(N(CC)CC)C.CCCCCCC>CN(C)C=O>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([OH:42])[CH2:38][CH2:37]3)=[O:33])=[N:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8900HeptaneHCID 695176994-(tert-Butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic Acid 5-benzoylamino-pyridin-2-yl EsterHCID 178522254HCID 178522254, Verbindung

Produkt 1

HCID 695188084-Hydroxy-piperidine-1-carboxylic Acid 5-(4-chloro-benzoylamino)-pyridin-2-yl EsterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 4-chloro-N-(6-hydroxy-pyridin-3-yl)-benzamide (0.50 g, 2.00 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-piperidine-1-carboxylic acid 5-benzoylamino-pyridin-2-yl ester (0.90 g, 2.00 mmol) and triethylamine (0.20 g, 2.00 mmol) in dimethylformamide (10 mL) was stirred overnight at room temperature. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane, filtered over a short pad of silicagel and washed with ethyl acetate:heptane 50:50. The solvent was evaporated in vacuo and the residue was redissolved in acetonitrile and hydrofluoric acid (min. 40% in water, 0.50 mL) was added. After stirring overnight at room temperature the solvent was evaporated in vacuo. Dichloromethane and triethylamine (1 mL) were added and the solution was extracted twice with water, dried over sodium sulphate, filtered and evaporated in vacuo. Crystallisation from ethyl acetate:heptane yielded the title compound (321 mg, 43% yield).

Aufarbeitung

  1. customThe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. filtrationfiltered over a short pad of silicagel
  4. washwashed with ethyl acetate:heptane 50:50
  5. customThe solvent was evaporated in vacuo
  6. dissolutionthe residue was redissolved in acetonitrile
  7. additionhydrofluoric acid (min. 40% in water, 0.50 mL) was added
  8. customwas evaporated in vacuo
  9. additionDichloromethane and triethylamine (1 mL) were added
  10. extractionthe solution was extracted twice with water
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. customevaporated in vacuo
  14. customCrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-374da5f7e4e84adc86f050b695b91ce7
Quelldatensatz
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07067517B2

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