Hydrochloric Acid → HCID 16244454, Verbindung

HRID 560273Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 560273
B(F)(F)F.CCOCC.[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][C:20](=O)[NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13].[BH4-].[Na+].Cl.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH3:10][O:11][C:12]([C:14]1[C:23]2[O:22][CH2:21][CH2:20][NH:19][C:18]=2[CH:17]=[CH:16][CH:15]=1)=[O:13]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 23770643Methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylate

Produkt 1

HCID 16244454HCID 16244454, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Boron trifluoride diethyl etherate (10.1 mmol) is added dropwise to a mixture of 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-8-carboxylic acid methyl ester (4.83 mmol) in THF (12 mL) to keep the temperature below 5° C. After 20 min sodium borohydride (10.1 mmol) is added and the mixture is stirred at 5° C. for 60 min. EtOAc (6.0 mL) and aq. HCl (1.0 M, 6.0 mL) are added dropwise. The mixture is made basic by addition of sat. aq. NaHCO3 solution, the layers are separated and the aq. layer is extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by FC (heptane to heptane/EtOAc 3/7). LC-MS: tR=0.69 min; [M+H]+=194.0.

Aufarbeitung

  1. customthe temperature below 5° C
  2. customthe layers are separated
  3. extractionthe aq. layer is extracted with EtOAc
  4. dry with materialThe combined organic layers are dried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a2a9fc86b4094d5fa735a5ee8d72a3d4
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063099B2

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