Trifluoroacetic acid → HCID 178471612, Verbindung

HRID 852862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852862
[CH2:1]([O:3][C:4](=[O:41])[CH:5]=[CH:6][CH:7]([NH:33]C(OC(C)(C)C)=O)[CH2:8][C:9]1[N:10]=[CH:11][N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:13]=1)[CH3:2].C(O)(C(F)(F)F)=O>>[CH2:1]([O:3][C:4](=[O:41])[CH:5]=[CH:6][CH:7]([NH2:33])[CH2:8][C:9]1[N:10]=[CH:11][NH:12][CH:13]=1)[CH3:2]

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 694162234-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester

Produkt 1

HCID 178471612HCID 178471612, VerbindungAusbeute 53 %

Versuchsvorschrift

A representative procedure is as follows. 4-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester (100 mg, 0.181 mmol) was stirred with TFA (5 mL) overnight under an atmosphere of argon. The TFA was removed and the residue triturated with Et2O. The remaining solid was subject to preparative reverse phase HPLC (30% B to 100% B over 20 min) to yield after lyophilization a gum (20 mg, 53%). 1H NMR (300 MHz, d6-DMSO) δ 1.19 (3H, t, J=7.02), 3.19 (2H, br s), 4.12 (2H, q, J=7.02), 4.33 (1H, m), 6.09 (1H, d, J=15.87), 6.76 (1H, dd, J=7.14, 15.87), 7.49 (1H, br s), 9.01 (1H, br s). 13C NMR (d6-DMSO) δ 164.76, 141.83, 134.64, 127.39, 125.08, 118.09, 60.58, 50.03, 27.57, 14.06.

Aufarbeitung

  1. customThe TFA was removed
  2. customthe residue triturated with Et2O
  3. customwas subject to preparative reverse phase HPLC (30% B to 100% B over 20 min)

Quellen und Nachweise

ORD-Eintrag
ord-27124b55238d4ea281bf2ea94a942cda
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253194B2

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