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Benzoyl isothiocyanate → N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

HRID 930286
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 930286
Cl.[NH2:2][C@@:3]([C:12]1[CH:17]=[C:16]([Br:18])[CH:15]=[CH:14][C:13]=1[F:19])([CH3:11])[CH2:4][C@H:5]([OH:10])[C:6]([F:9])([F:8])[F:7].C(N(C(C)C)CC)(C)C.[C:29]([N:37]=[C:38]=S)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CCN=C=NCCC[N+](C)(C)C.[I-]>C1COCC1.CCOC(C)=O.CCCCCC>[Br:18][C:16]1[CH:15]=[CH:14][C:13]([F:19])=[C:12]([C@:3]2([CH3:11])[CH2:4][C@@H:5]([C:6]([F:7])([F:8])[F:9])[O:10][C:38]([NH:37][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:2]2)[CH:17]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 68284Benzoyl isothiocyanateHCID 81531DiisopropylethylamineHCID 1222421-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide methiodideHCID 86732117(2S,4S)-4-amino-4-(5-bromo-2-fluorophenyl)-1,1,1-trifluoropentan-2-ol hydrochloride

Produkt 1

HCID 86732116N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide
Ausbeute 90,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of (2S,4S)-4-amino-4-(5-bromo-2-fluorophenyl)-1,1,1-trifluoropentan-2-ol hydrochloride (4f, 693 mg, 1.890 mmol) in THF (10 mL) was treated with diisopropylethylamine (Aldrich; 823 μL, 4.73 mmol) and stirred for 5 min. Benzoyl isothiocyanate (Aldrich; 280 μL, 2.083 mmol) was added dropwise and the reaction mixture was stirred for 3 h. The reaction mixture was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide methiodide (Aldrich; 674 mg, 2.270 mmol) and heated to 70° C. for 2 h and subsequently to 50° C. for 16 h. The reaction mixture was concentrated and extracted into EtOAc from saturated brine. The combined organic extracts were dried over MgSO4, concentrated, and purified by flash chromatography on silica gel (Gradient: 0%→25% EtOAc/hexane to give N-((4S,6S)-4-(5-bromo-2-fluorophenyl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (789 mg, 1.718 mmol) as a white solid. MS m/z=460.9 [M+H]+. Calculated for C19H15BrF4N2O2: 459.2

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted into EtOAc from saturated brine
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (Gradient

Quellen und Nachweise

ORD-Eintrag
ord-0d4b42e25a614545997b2232249e71f8
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09296734B2

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