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tert-Butyl mercaptan → (5-{4-tert-Butylsulfanyl-2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid

HRID 554639
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 554639
[H-].[Na+].[CH3:3][C:4]([SH:7])([CH3:6])[CH3:5].C([O:10][C:11](=[O:35])[CH2:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:19]2[CH:24]=[CH:23][C:22](F)=[CH:21][C:20]=2[CH2:26][N:27]([C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])[CH2:28][CH3:29])[CH:18]=1)C>CN(C=O)C.O.N#N>[C:4]([S:7][C:22]1[CH:23]=[CH:24][C:19]([C:17]2[CH:18]=[C:13]([CH2:12][C:11]([OH:35])=[O:10])[CH:14]=[N:15][CH:16]=2)=[C:20]([CH2:26][N:27]([C:30]([CH:32]2[CH2:34][CH2:33]2)=[O:31])[CH2:28][CH3:29])[CH:21]=1)([CH3:6])([CH3:5])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 6387tert-Butyl mercaptanHCID 24758Sodium hydrideHCID 58565012(5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Produkt 1

HCID 45138778(5-{4-tert-Butylsulfanyl-2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-phenyl}-pyridin-3-yl)-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 947
Nitrogen
Lösungsmittel
HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60% in mineral oil; 0.042 g, 1.04 mmol) was suspended in DMF (5 mL). After stirring for 10 minutes, 2-methyl-2-propanethiol (0.13 mL, 1.15 mmol) was added, and the mixture was stirred for 30 minutes. (5-{2-[(N-Cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-fluoro-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.20 g, 0.52 mmol) was added, and the reaction was stirred at 90° C. overnight. The mixture was diluted with H2O, and N2 was bubbled through the solution into a bleach trap until all odor was removed. The aqueous layer was washed with EtOAc, and then acidified to pH 4 and extracted with EtOAc. The combined organic layers were concentrated, and the residue was purified by preparative HPLC to give Compound 22.

Aufarbeitung

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringthe reaction was stirred at 90° C. overnight
  3. customwas bubbled through the solution into a bleach trap until all odor
  4. customwas removed
  5. washThe aqueous layer was washed with EtOAc
  6. extractionextracted with EtOAc
  7. concentrationThe combined organic layers were concentrated
  8. customthe residue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d857485f4ea04e04a8c56b161bd5d003
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08049015B2

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