Trifluoroacetohydrazide → HCID 89414355, Verbindung

HRID 1429414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1429414
[CH2:1]([C@@H:8]1[CH2:15][CH2:14][CH2:13][NH:12][C:11](=S)[CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]([C:35]([NH:37][NH2:38])=O)([F:34])([F:33])[F:32].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1.CCOCC.C1(C)C=CC=CC=1.O.CC(=O)OCC.[Hg](OC(C)=O)OC(C)=O>[CH2:1]([C@@H:8]1[CH2:15][CH2:14][CH2:13][N:12]2[C:35]([C:31]([F:34])([F:33])[F:32])=[N:37][N:38]=[C:11]2[CH2:10][N:9]1[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[O:26][C:27]([F:30])([F:29])[F:28])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 3

HCID 229753TrifluoroacetohydrazideHCID 521998p-Toluenesulfonic acid monohydrateHCID 86677168HCID 86677168, Verbindung

Produkt 1

HCID 89414355HCID 89414355, VerbindungAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 16683746DiacetyloxymercuryKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

A solution of compound 31n (150 mg, 0.33 mmol) in THF (15 mL) was cooled to 0° C., treated with Hg(OAc)2 (118 mg, 0.36 mmol) and CF3CONHNH2 (173 mg, 1.65 mmol), stirred for 2 h, diluted with Et2O (20 mL), filtered through Celite and evaporated. A solution of the residue in toluene/H2O (30:1, 15 mL) was treated with TsOH.H2O (250 mg, 1.32 mmol) and stirred at 75° C. for 12 h. The mixture was diluted with EA (30 mL) and washed with saturated K2CO3. The aqueous layer was extracted with EA (20 mL). The combined organic layers were dried over Na2SO4. After filtration, the filtrate was evaporated and the residue was purified by Preparative HPLC to give compound 31 as a white solid (113 mg, 64% yield). 1H NMR (500 MHz, CDCl3) δ 8.14 (d, J=7.5 Hz, 1H), 7.68 (t, J=8.5 Hz, 1H), 7.50 (t, J=7.5 Hz, 1H), 7.40 (d, J=8.5 Hz, 1H), 7.15-7.10 (m, 3H), 6.76-6.70 (m, 2H), 5.71 (d, J=18.0 Hz, 1H), 4.97 (m, 1H), 4.90 (d, J=8.0 Hz, 1H), 4.26 (dd, J=15.0, 8.0 Hz, 1H) 4.21 (m, 1H), 2.59 (dd, J=13.0, 10.5 Hz, 1H), 2.33 (dd, J=13.0, 5.0 Hz, 1H), 2.12-1.90 (m, 2H), 1.70-1.60 (m, 2H). MS (ESI+) m/z: 535 [M+H]+.

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customevaporated
  3. stirringstirred at 75° C. for 12 h
  4. washwashed with saturated K2CO3
  5. extractionThe aqueous layer was extracted with EA (20 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationAfter filtration
  8. customthe filtrate was evaporated
  9. customthe residue was purified by Preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d5a9a8fe80694e6486480c3ba25ea9e2
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940722B2

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