2-Bromo-4-phenylcyclohexan-1-one → HCID 68647835, Verbindung

HRID 1162588Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162588
Br[CH:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][C:3]1=O.[C:15]([O:19][C:20](=[O:32])[CH2:21][CH2:22][N:23]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:24]([NH2:26])=[S:25])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20](=[O:32])[CH2:21][CH2:22][N:23]([CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:24]1[S:25][C:2]2[CH2:7][CH:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][C:3]=2[N:26]=1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

4

Edukt 2

HCID 132483272-Bromo-4-phenylcyclohexan-1-oneHCID 86601761HCID 86601761, Verbindung

Produkt 1

HCID 68647835HCID 68647835, VerbindungAusbeute 98,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The 2-bromo-4-phenylcyclohexanone (2.30 mmol) and 3-(1-Cyclopentyl-thioureido)-propionic acid tert-butyl ester (257 mg, 0.945 mmol) were combined as in general procedure B (13 mL THF, 40° C., 15 h). After aqueous workup, the crude product was purified by silica gel chromatography (gradient, hexane→10% EtOAc-hexane) to afford 3-[cyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid tert-butyl ester (398 mg). The ester was dissolved in CH2Cl2 (2 mL) and TFA (2 mL) was added. The reaction mixture was stirred at room temperature, until the starting material, was consumed by TLC. The volatiles were removed and the residue was dissolved in MeOH. NaOH solution (0.90 mmol) was added followed by half-saturated NaCl (20 mL). The aqueous layer was extracted with CH2Cl2 (3×15 mL) and dried over MgSO4 to provide 3-[Cyclopentylcyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid. The sodium salt was prepared by general procedure J and triturated with hexane to yield 3-[cyclopentyl-(6-phenyl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-amino]-propionic acid, sodium salt (336 mg) LCMS m/z: 372 (M+1)+.

Aufarbeitung

  1. customAfter aqueous workup, the crude product was purified by silica gel chromatography (gradient, hexane→10% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-172a384cc720402db10f86d6ed56fa20
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820704B2

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