Sodium Bicarbonate → Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylate

HRID 43660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 43660
[C:1]([N:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:6]([O:21][CH2:22][CH2:23][CH3:24])[CH2:5]1)(=[O:3])[NH2:2].Br[CH:26]([CH2:36][CH3:37])[C:27](=O)[C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29].C(=O)(O)[O-].[Na+]>C1COCC1>[CH2:13]([O:12][C:11]([NH:10][C@H:7]1[CH2:8][CH2:9][N:4]([C:1]2[O:3][C:26]([CH2:36][CH3:37])=[C:27]([C:28]([O:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:29])[N:2]=2)[CH2:5][C@H:6]1[O:21][CH2:22][CH2:23][CH3:24])=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 86648534Butyl 3-bromo-2-oxopentanoateHCID 131730866HCID 131730866, Verbindung

Produkt 1

HCID 86648605Butyl cis(+/-)-2-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)-5-ethyl-1,3-oxazole-4-carboxylateAusbeute 86,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The same operation as in Example (103c) was performed using cis(±)-benzyl (1-carbamoyl-3-propoxypiperidin-4-yl)carbamate obtained in Example (113f) (0.80 g, 2.39 mmol), butyl 3-bromo-2-oxopentanoate obtained in Example (110a) (4 g, 15.9 mmol), sodium bicarbonate (0.7 g, 8.33 mmol) and THF (15 mL). The resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1) to obtain 1.01 g of the title compound as a light brown oily substance (87%).

Aufarbeitung

  1. customThe resulting residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane=1/10, 1/2, 1/1, 2/1, 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-c6d0f9e0067a4cd6b44ac42aecf0e016
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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