Trifluoroacetic acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

HRID 1037407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1037407
FC(F)(F)C(O)=O.C(OC([NH:15][C:16]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18][CH2:17]1)=O)(C)(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:15][C:16]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[C:35](=[O:36])[C:34]4[C:29](=[C:30]([C:37]([OH:39])=[O:38])[CH:31]=[CH:32][CH:33]=4)[O:28][C:27]=3[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:24][CH:25]=2)[CH2:17][CH2:18][CH2:19]1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acid2×HCID 670678653-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

Produkt 1

HCID 670679903-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acidAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

trifluoro-acetic acid: 3-[4-(1-tert-Butoxycarbonylamino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid (18 mg, 0.035 mmol) was treated with a solution of 25% TFA in DCM (4 mL) and stirred at RT for 1 h. The reaction mixture was diluted with toluene and concentrated in vacuo. The resultant residue was triturated with diethyl ether and DCM, and concentrated in vacuo to give the title compound as a light tan solid (10 mg, 54%). 1H NMR (400 MHz, DMSO-d6): δ 13.44 (bs, 1H), 8.44 (s, 3H), 8.28-8.23 (m, 2H), 7.57 (t, J=7.7 Hz, 1H), 7.48-7.36 (m, 5H), 7.33-7.27 (m, 4H), 2.64-2.53 (m, 2H), 2.51-2.42 (m, 2H), 2.18-2.05 (m, 1H), 1.85-1.73 (m, 1H). LCMS (Method E): RT=2.89 min, [M+H]+=412.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was triturated with diethyl ether and DCM
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3130de00525c43d3b35e2a12ea873bf4
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546376B2

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