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Tetrabutylammonium Fluoride → HCID 145857714, Verbindung

HRID 2216154
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2216154
C[Si](C)(C)CCOC(=O)[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([C:24]3[CH:28]=[C:27]([C:29]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[NH:30])[S:26][C:25]=3[S:39][CH3:40])(=[O:23])=[O:22])[CH:16]=2)=[C:10]([NH2:41])[CH:9]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:35]([O:34][C:32](=[O:33])[NH:31][C:29]([C:27]1[S:26][C:25]([S:39][CH3:40])=[C:24]([S:21]([C:17]2[CH:16]=[C:15]([C:11]3[C:12]([CH3:14])=[CH:13][C:8]([NH2:7])=[CH:9][C:10]=3[NH2:41])[CH:20]=[CH:19][CH:18]=2)(=[O:22])=[O:23])[CH:28]=1)=[NH:30])([CH3:37])([CH3:38])[CH3:36]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 145857641HCID 145857641, Verbindung

Produkt 1

HCID 145857714HCID 145857714, VerbindungAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

{2-Amino-3′-[5-(tert-butoxycarbonylamino-imino-methyl)-2-methylsulfanyl-thiophene-3-sulfonyl]-6-methyl-biphenyl-4-yl}-carbamic acid 2-trimethylsilanyl-ethyl ester (1000 mg, 1.48 mmol, Example 294, step f) was dissolved into THF (25 mL). To this was added TBAF (1M, 1.62 mL, 1.62 mmol) and the reaction was warmed to 40° C. with stirring for 3 hours. Additional TBAF (1.48 mL, 1.48 mmol) was added and the reaction was stirred at rt overnight. The solvents were removed in vacuo, the residue was dissolved into EtOAc and washed with water several times (5 washes). The combined organic layers were dried (MgSO4) and the solvents were removed in vacuo resulting in the title compound as a yellow solid (800 mg, 100%). 1H-NMR (CDCl3): δ: 8.03 (s, 1H), 7.95–7.93 (m, 1H), 7.89–7.88 (m, 1H), 7.59–7.53 (m, 2H), 6.08 (m, 1H), 5.99 (m, 1H), 2.55 (s, 3H), 1.85 (s, 3H), 1.52 (s, 9H).

Aufarbeitung

  1. stirringthe reaction was stirred at rt overnight
  2. customThe solvents were removed in vacuo
  3. dissolutionthe residue was dissolved into EtOAc
  4. washwashed with water several times (5 washes)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. customthe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6343862bdcdf4c8eb9300f5da1c16ce7
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109354B2

Notizen zur Reaktion

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