Hydrochloric Acid → HCID 23456812, Verbindung

HRID 1874952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874952
CC([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15](C(OCCC(C)(C)C)=O)[C:14]([C:28]([O-:30])=[O:29])=[CH:13]2)(C)C.Cl.[C:34](O)([C:36](F)(F)F)=O>C1COCC1>[OH:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([C:28]([O:30][CH2:34][CH3:36])=[O:29])=[CH:13]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 86761647HCID 86761647, Verbindung

Produkt 1

HCID 23456812HCID 23456812, VerbindungAusbeute 107 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-(1,1-dimethylethyl)2-ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-1,2-dicarboxylate (0.389 g, 0.840 mmol) in THF (4 mL) was treated with 1N HCl (0.840 mL, 0.840 mmol) and the reaction mixture was stirred for several hours at room temp. TLC showed consumption of the starting material and 2 product spots. Solvents were evaporated and the residue dissolved in DCM (4 mL) and TFA (0.25 mL, 3.24 mmol) was added. TLC showed a single product spot. The solvents were evaporated to afford the title compound (0.224 g, 96%) as a grey solid. 1H NMR (400 MHz, Acetone-d6) δ ppm 10.74 (br. s., 1H), 7.41 (d, 1H), 7.32 (s, 1H), 7.12 (d, 1H), 7.06 (d, 1H), 6.94 (dd, 1H), 4.32 (q, 2H), 4.05 (t, 2H), 3.88 (t, 2H), 1.32 (t, 3H). LCMS: m/z 204.2 (M-45).

Aufarbeitung

  1. customconsumption of the starting material and 2 product spots
  2. customSolvents were evaporated
  3. dissolutionthe residue dissolved in DCM (4 mL)
  4. customThe solvents were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-9b701ef67a574488ad52ec40b06e884a
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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