Trifluoroacetic acid → 3-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid

HRID 1181132Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1181132
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:50])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[CH:18][C:17]=1[CH2:39][O:40][C:41](=[O:49])[NH:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)(C)(C)C>C(Cl)Cl>[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH2:23][O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][C:13]([OH:50])=[O:12])=[C:17]([CH2:39][O:40][C:41](=[O:49])[NH:42][CH:43]3[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]3)[CH:18]=2)=[CH:28][CH:29]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 589791993-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester

Produkt 1

HCID 179845663-{4-[3-(Biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acidAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (0.032 mL, 0.42 mmol) was added to a solution of 3-{4-[3-(biphenyl-4-yloxy)-propoxy]-2-cyclohexylcarbamoyloxymethyl-phenyl}-propionic acid tert-butyl ester (50 mg, 0.085 mmol) in CH2Cl2 (5 mL) at room temperature. The reaction mixture was stirred overnight and concentrated under vacuum to give the title compound (41 mg, 90%). 1H-NMR (200 MHz, CDCl3): δ 9.4 (br s, 1H), 7.58-7.49 (m, 4H), 7.42 (m, 2H), 7.32 (m, 1H), 7.13 (d, 1H, J=8.3), 7.00-6.93 (m, 3H), 6.84 (dd, 1H, J=7.8, 2.7), 5.11 (s, 2H), 4.76 (br s, 1H), 4.17 (m, 4H), 3.57-3.35 (m, 1H), 2.95 (t, 2H, J=7.8), 2.63 (t, 2H, J=7.8), 2.27 (qn, 2H, J=6.0), 1.99-1.05 (m, 10H).

Aufarbeitung

  1. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-4bd8bb2379664979aa98cd209b1ccead
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282501B2

Notizen zur Reaktion

Wird geladen…