Hydrochloric Acid → 6-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid

HRID 1697455Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1697455
C([O:3][C:4]([CH:6]1[CH2:11][NH:10][C:9]2[CH:12]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:14]=[CH:15][C:8]=2[O:7]1)=[O:5])C.[OH-].[Na+].ClC(OCC1C=CC=CC=1)=O.Cl>O1CCOCC1.O>[F:19][C:16]([F:17])([F:18])[C:13]1[CH:14]=[CH:15][C:8]2[O:7][CH:6]([C:4]([OH:5])=[O:3])[CH2:11][NH:10][C:9]=2[CH:12]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 11747775ethyl 6-(trifluoromethyl)-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Produkt 1

HCID 203952756-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acidAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

6-Trifluoromethyl-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid ethyl ester (500 mg, 2 mmol) was dissolved in 1,4-dioxane (20 mL). Sodium hydroxide (109 mg, 2.7 mmol) was added, followed by benzyl chloroformate (311 μL, 2.2 mmol), and the reaction stirred overnight at room temperature. The reaction mixture was acidified with 2N HCl and diluted with water (20 mL), then extracted with EtOAc (3×30 mL). The combined organics were washed with brine (2×40 mL), dried (MgSO4), filtered and concentrated. Trituration using DCM/hexanes gave the title compound (330 mg, 10%) as a pale brown solid. m/z=245.7 (M−1), r.t.=2.78 mins. 1H NMR (400 MHz; CDCl3) δ 7.01 (2H, s), 6.86 (1H, s), 4.94 (1H, t), 3.66 (2H, dd).

Aufarbeitung

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined organics were washed with brine (2×40 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d7c2fc7dd43a4f0a9cbda37a77f43de0
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163901B2

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