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4-Methylmorpholine → Tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate

HRID 977211
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 977211
CN1CCOCC1.[O:8]=[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][CH:23]([C:25]([OH:27])=O)[O:22][C:21]3=[O:28])=[CH:16][CH:15]=2)[NH:10]1.[NH:29]1[CH2:34][CH2:33][CH:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.O>[O:8]=[C:9]1[O:13][N:12]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([N:20]3[CH2:24][CH:23]([C:25]([N:29]4[CH2:34][CH2:33][CH:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[O:27])[O:22][C:21]3=[O:28])=[CH:18][CH:19]=2)[NH:10]1
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Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 1512676Tert-butyl Piperidine-4-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1360051203-[4-(5-Oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid

Produkt 1

HCID 136146332
Tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3.03 g of N-methylmorpholine are added to a solution of 2.91 g of 3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinecarboxylic acid [obtainable according to Example 3], 2.77 g of tert-butyl piperidine-4-carboxylate, 2.02 g of 1-hydroxybenzotriazole and 2.86 g of N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride in 20 ml of DMF, and the mixture is stirred at room temperature for 5 h. 200 ml of water are subsequently added dropwise with intensive stirring, the crystalline precipitate formed is separated off and taken up in 90 ml of dichloromethane, and the mixture is dried over Na2SO4. The solution is concentrated in vacuo, and the resulting oil is triturated with diethyl ether to give tert-butyl 1-{3-[4-(5-oxo-1,2,4-oxadiazolin-3-yl)phenyl]-2-oxo-5-oxazolidinylcarbonyl}piperidine-4carboxylate, m.p. 171°-175°.

Aufarbeitung

  1. customthe crystalline precipitate formed
  2. customis separated off
  3. dry with materialthe mixture is dried over Na2SO4
  4. concentrationThe solution is concentrated in vacuo
  5. customthe resulting oil is triturated with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e5b269ecef6f44c49d858bc5c9cc014d
Quelldatensatz
uspto-grants-1997_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05614535

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