Triethylamine → HCID 86592945, Verbindung

HRID 1245398Notizen

Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:30])[CH:4]=[CH:5][CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1.[C:31]([OH:34])(=[S:33])[CH3:32].C(N(CC)CC)C>>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH:5]([S:33][C:31](=[O:34])[CH3:32])[CH:6]1[O:10][N:9]=[C:8]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[C:21]([CH3:29])[CH:20]=3)=[CH:13][CH:12]=2)[CH2:7]1

Komponenten

Edukt 3

HCID 8471Triethylamine

HCID 69640073HCID 69640073, Verbindung

HCID 178418634HCID 178418634, Verbindung

Produkt 1

HCID 86592945HCID 86592945, VerbindungAusbeute 63 %

Versuchsvorschrift

A suspension of the product from step 11a (1.0 g, 2.5 mmol), thioacetic acid (3.0 mL), and triethylamine (0.25 mL, 1.8 mmol) was stirred for 6 h at room temperature while slowly becoming a clear solution. The reaction was partitioned between ethyl acetate and water. The organic layer was washed with aqueous sodium bicarbonate (2×), brine, dried over magnesium sulfate, and concentrated to give the crude product. This was purified by FCC on silica gel eluting ethyl acetate:hexanes (gradient) to give 3-acetylsulfanyl-3-{3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-propionic acid methyl ester (0.74 g, 63%) as an oil. MS found: (M+H)+=479.

Aufarbeitung

customThe reaction was partitioned between ethyl acetate and water
washThe organic layer was washed with aqueous sodium bicarbonate (2×), brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto give the crude product
customThis was purified by FCC on silica gel
washeluting ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-d1e9e5bb369e4743a6a550c16ce11e28
Quelldatensatz: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07125870B2

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