Trifluoroacetic acid → HCID 75053846, Verbindung

HRID 531382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 531382
[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:59])[N:24](CC5C=CC(OC)=CC=5)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:42][S:43]([C:46]6([CH3:49])[CH2:48][CH2:47]6)(=[O:45])=[O:44])=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:62])[C:13]([O:60][CH3:61])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[CH:1]([C:4]1[N:5]=[C:6]([C:9]2[CH:18]=[C:17]([O:19][CH:20]3[CH2:38][CH:37]4[N:22]([C:23](=[O:59])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:42][S:43]([C:46]6([CH3:49])[CH2:48][CH2:47]6)(=[O:45])=[O:44])=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:21]3)[C:16]3[C:11](=[C:12]([CH3:62])[C:13]([O:60][CH3:61])=[CH:14][CH:15]=3)[N:10]=2)[S:7][CH:8]=1)([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 76674797HCID 76674797, Verbindung

Produkt 1

HCID 75053846HCID 75053846, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To compound 139 (106 mg, 0.120 mmol) dissolved in dichloromethane (18 mL) were added triethylsilane (38 μL, 0.240 mmol) and TFA (9 mL) and the reaction mixture was stirred at room temperature for 1 hour. The solvents were evaporated and co-evaporated trice with toluene. The residue was dissolved in dichloromethane and the organic phase was washed twice with saturated NaHCO3 solution. The organic phase was dried, filtered, and concentrated and the crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1) to yield the title compound (73 mg, 80%) as a slightly yellow solid. LC-MS purity: >95%. (M+H)+ cald: 765.3. found: 765.7.

Aufarbeitung

  1. customThe solvents were evaporated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe organic phase was washed twice with saturated NaHCO3 solution
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe crude product was purified by flash column chromatography (toluene/ethyl acetate 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-3a59d35be23e4f9ab5f00eded0c3595e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353103B2

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