Methanol → tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamate

HRID 16356

Reaktionsgleichung

Reaktionsgleichung von HRID 16356
C(=O)([O-])[O-].[K+].[K+].CO.C1COCC1.[C:14]([O:18][C:19]([NH:21][C@H:22]([C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[C:39]([F:45])[CH:38]=1)[C@H:23]([O:25]C(=O)C1C=CC([N+]([O-])=O)=CC=1)[CH3:24])=[O:20])([CH3:17])([CH3:16])[CH3:15]>O.C(OCC)(=O)C>[C:14]([O:18][C:19](=[O:20])[NH:21][C@H:22]([C:37]1[CH:42]=[C:41]([F:43])[C:40]([F:44])=[C:39]([F:45])[CH:38]=1)[C@H:23]([OH:25])[CH3:24])([CH3:15])([CH3:16])[CH3:17]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 68911294[(1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl]4-nitrobenzoate

Produkt 1

HCID 68717986tert-butyl [(1R,2R)-2-hydroxy-1-(3,4,5-trifluorophenyl)propyl]carbamateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A potassium carbonate powder (6.43 g) was added to a solution mixture of methanol (90 mL) and THF (10 mL) of 4-nitrobenzoic acid (1R,2R)-2-tert-butoxycarbonylamino-1-methyl-2-(3,4,5-trifluorophenyl)ethyl ester (7.03 g). The resulting reaction solution was stirred at room temperature for 1 hr, and ethyl acetate and water were added thereto. The organic layer was separated, washed with saturated saline twice, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the obtained residue, diethylether was added. The insoluble matter was removed by filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1) to give 4.49 g of the title compound. The physical property values of this compound were as follows:

Aufarbeitung

  1. customThe resulting reaction solution
  2. customThe organic layer was separated
  3. washwashed with saturated saline twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue, diethylether was added
  7. customThe insoluble matter was removed by filtration
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography (toluene:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-a8f4e62a5cd14e3b94a24f41ed5e48fb
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737141B2

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