Trifluoroacetic acid → Dimethyl {[({[4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl) oxy]methyl}phosphonate

HRID 1013535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1013535
C(OC([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:40]=[CH:39][C:26]([CH2:27][NH:28][C:29]([O:31][CH2:32][P:33](=[O:38])([O:36][CH3:37])[O:34][CH3:35])=[O:30])=[CH:25][CH:24]=1)=[O:22])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[CH:11][C:10]=1[NH:20][C:21]([C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:28][C:29]([O:31][CH2:32][P:33](=[O:38])([O:36][CH3:37])[O:34][CH3:35])=[O:30])=[CH:39][CH:40]=1)=[O:22]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57925842Dimethyl {[({[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl)oxy]methyl}phosphonate

Produkt 1

HCID 57925826Dimethyl {[({[4-({[2-amino-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl) oxy]methyl}phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Dimethyl {[({[4-({[2-[(tert-butoxycarbonyl)amino]-5-(2-thienyl)phenyl]amino}carbonyl)benzyl]amino}carbonyl)oxy]methyl}phosphonate 0.496 g, 0.841 mmol) was dissolved in DCM (4 ml). TFA (1 ml, 12.98 mmol) was added. The reaction was allowed to stir for ˜1 h 15 min. The reaction was diluted with DCM and washed with saturated aqueous sodium hydrogen carbonate. The aqueous layer was extracted three times with DCM. The combined organic layers were dried over Na2SO4, filtered, and concentrated. 1H NMR (DMSO-d6, 600 MHz) δ 9.67 (s, 1H), 8.13 (t, J=6.3 Hz, 1H), 7.93 (d, J=7.9 Hz, 2H), 7.44 (bs, 1H), 7.35 (d, J=7.9 Hz, 2H), 7.32 (dd, J=5.1 Hz, 1.0 Hz, 1H), 7.26 (dd, J=8.4 Hz, 2.2 Hz, 1H), 7.21 (d, J=3.1 Hz, 1H), 7.01 (dd, J=5.1 Hz, 3.7 Hz, 1 H), 6.77 (d, J=8.2 Hz, 1H), 5.11 (s, 2H), 4.39 (d, J=7.9 Hz, 2H), 4.25 (d, J=6.2 Hz, 2H), 3.66 (d, J=10.6 Hz, 6H). MS: calc'd 490 (MH+), exp 490 (MH+).

Aufarbeitung

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. extractionThe aqueous layer was extracted three times with DCM
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-11340297368c4fd4b2688596283bb51f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981874B2

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