Hydrochloric Acid → HCID 68647842, Verbindung

HRID 1162582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162582
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[S:13][CH:14]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[H-].[Na+:23].[OH-:24].[Na+].Cl.[CH3:27][OH:28]>C1COCC1>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]([N:15]([CH2:16][C:17]3[S:18][CH:19]=[CH:20][CH:21]=3)[CH2:2][CH2:1][CH2:4][CH2:5][C:27]([O-:28])=[O:24])[S:13][CH:14]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2].[Na+:23]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 24730368HCID 24730368, Verbindung

Produkt 1

HCID 68647842HCID 68647842, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To the THF solution of [4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amine (150.0 mg, 0.5 mmol) and methyl 5-bromopentaoate (215 μL, 0.1.5 mmol) was added NaH (60 mg, 60%, 0.1.5 mmol) and the resulting mixture was heated at 60° C. for 5 h, after cooling to room temperature methanol (2.0 ml). NaOH (2.0 ml, 1.0 M) added and mix was stirred at room temperature for 15 h. HCl added dropwise to pH 7.0. The acid was extracted with EtOAc (2×20 ml), combined organic extracts dried (Na2SO4), filtered, concentrated, and purified on silica gel column. The sodium salt was made following procedure J to afford the sodium 5-{[4-(4-isopropyl-phenyl)-thiazol-2-yl]-thiophen-2-ylmethyl-amino}-pentanoate (110 mg). LCMS m/z: 416 (M+1)+.

Aufarbeitung

  1. additionmix
  2. extractionThe acid was extracted with EtOAc (2×20 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-e5b120a1e9714cc59d3099688d96a3d9
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820704B2

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