3-Heptanone → 2-(s)-(1-Propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide

HRID 131656

Reaktionsgleichung

Cl.C[O:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH2:21])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9].[CH3:25][CH2:26][C:27](=O)[CH2:28][CH2:29][CH2:30][CH3:31].S([O-])([O-])(=O)=O.[Na+].[Na+].C([BH3-])#N.[Na+]>ClC(Cl)C.CO.C(O)(=O)C>[OH:3][C:4]([CH3:24])([CH3:23])[CH2:5][CH2:6][CH2:7][CH:8]([C:10]1[S:14][C:13]([NH:15][C:16](=[O:22])[C@@H:17]([NH:21][CH:28]([CH2:29][CH2:30][CH3:31])[CH2:27][CH2:26][CH3:25])[CH2:18][CH2:19][CH3:20])=[N:12][CH:11]=1)[CH3:9]

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

A mixture of 2-(S)-amino-pentanoic acid [5-(5-methoxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide HCl salt (100 mg, 0.265 mmol) and 3-heptanone (0.1 mL), acetic acid (0.2 mL), sodium sulfate and sodium cyanoborohydride (100 mg) in dichloroethane (2 mL) and methanol (1 mL) was stirred at 40° C. overnight. The mixture was quenched with water, basified by dilute sodium hydroxide, and extracted with methylene chloride. The organic layer was concentrated to dryness. The residue was purified by Biotage silica gel column chromatography to isolate 2-(S)-(1-propyl-butylamino)-pentanoic acid [5-(5-hydroxy-1,5-dimethyl-hexyl)-thiazol-2-yl]-amide as a colorless oil, LC-MS, RT=2.2 min, M+1=426.5.

Aufarbeitung

customThe mixture was quenched with water
extractionextracted with methylene chloride
concentrationThe organic layer was concentrated to dryness
customThe residue was purified by Biotage silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-59679df6d87c47658f1cf87b4a0d71bc
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07384968B2

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