Tetrahydrofuran → HCID 21072811, Verbindung

HRID 1372919Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1372919
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:20](=[O:26])[CH:21](OCC)O)[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]1[C:36]2[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=2[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]1=[O:46].C1COCC1.[BH4-].[Li+]>O.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:20]([OH:26])[CH2:21][NH:27][C:28]([CH3:48])([CH3:47])[CH2:29][CH2:30][N:31]2[C:36]3[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=3[C:34]([CH2:44][CH3:45])([CH2:42][CH3:43])[O:33][C:32]2=[O:46])[C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21072818HCID 21072818, VerbindungHCID 22063474HCID 22063474, Verbindung

Produkt 1

HCID 21072811HCID 21072811, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A solution of 232 mg (0.649 mmol) 6-benzyloxy-8-(2-ethoxy-2-hydroxy-acetyl)-4H-benzo[1,4]oxazin-3-one and 200 mg (0.649 mmol) 1-(3-amino-3-methyl-butyl)-4,4-diethyl-7-fluoro-1,4-dihydro-benzo[d][1,3]oxazin-2-one in abs. THF (5 mL) is stirred for 2.5 h at RT. The mixture is cooled to 5° C., combined with 60 mg (2.755 mmol) lithium borohydride, heated to RT and stirred for 1 h. The mixture is again cooled to 5° C. and slowly diluted with 15 ml water and 20 mL dichloromethane. The phases are separated and the aqueous phase is extracted with dichloromethane. The combined org. phases are dried with sodium sulphate and concentrated by evaporation in vacuo. The residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5).

Aufarbeitung

  1. temperatureheated to RT
  2. temperatureThe mixture is again cooled to 5° C.
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane
  5. dry with materialphases are dried with sodium sulphate
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe residue is purified by column chromatography (silica gel, dichloromethane/MeOH 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-1ff931f201fe4d84abd6d0b62eaba292
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160882B2

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