Diethylamine → (S)-4-[4-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-butyl]-2-methyl-3-oxo-piperazine-1-carbothioic acid O-naphthalen-2-yl ester

HRID 655584Notizen

Reaktionsgleichung

[OH:1][C@@H:2]1[CH2:9][N:8]([CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][C@@H:16]([CH3:20])[C:15]2=[O:21])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.Cl[C:23]([O:25][C:26]1[CH:35]=[CH:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=1)=[S:24].C(N(CC)CC)C.C(NCC)C>O1CCCC1>[CH:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:34]=[CH:35][C:26]=1[O:25][C:23]([N:17]1[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][CH2:10][N:8]2[CH2:7][CH2:6][C:3]3([CH2:4][CH2:5]3)[C@H:2]([OH:1])[CH2:9]2)[C:15](=[O:21])[C@@H:16]1[CH3:20])=[S:24]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (S)-1-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-butyl]-3-methyl-piperazin-2-one (intermediate 27; 50 mg, 0.17 mmol) in tetrahydrofuran (0.5 mL) was added at 0° C. O-2-naphthyl chlorothioformate (38 mg, 0.17 mmol) and triethylamine (17 mg, 0.17 mmol). The ice bath was removed, then after 20 min the reaction mixture was cooled to 0° C. and treated with diethylamine (6 mg, 90 μmol), then concentrated under vacuum. Chromatography (SiO2; dichloromethane/methanol/25% aq. ammonia solution 90:10:0.25) furnished the title compound (52 mg, 64%). Orange oil, MS (ISP)=482.4 (M+H)+.

Aufarbeitung

customThe ice bath was removed
concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag: ord-26a5644c2e9941089deeadf01dcfc19d
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08071586B2

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