Trifluoroacetic acid → (S)-7-Nitro-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 339252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339252
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][C@@H:9]([C:21](=[O:33])[NH:22][C@H:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)[N:10](C(OC(C)(C)C)=O)[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][C@@H:9]([C:21]([NH:22][C@H:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)=[O:33])[NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86705876(S)-tert-butyl 7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate2×

Produkt 1

HCID 86705890(S)-7-Nitro-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxamideAusbeute 97,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-tert-butyl 7-nitro-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Compound C of Example 20, 4.45 g, 9.86 mmol) in CH2Cl2 (49 mL) was added TFA (11.4 mL, 148 mmol). The resulting solution was stirred at room temperature for 1 h and then quenched carefully with sat. NaHCO3 until bubbling ceased. The aqueous layer was extracted with CH2Cl2 (3×), and the combined organic extracts were washed with sat. NaHCO3, water and sat. NaCl. The extracts were dried over Na2SO4, filtered and concentrated in vacuo to give 3.38 g of the title compound as a pale yellow solid. 1H NMR (CDCl3, mixture of amide rotamers) δ 8.05 (d, J=6.6 Hz, 1H), 7.97-7.88 (m, 1H), 7.53-7.32 (m, 2H), 7.22-6.94 (m, 4H), 5.25-5.03 (m, 1H), 4.18-3.94 (m, 2H), 3.83-3.65 (m, 1H), 3.35 (dd, J=16.7, 5.1 Hz, 1H), 3.09 (dd, J=17.1, 9.1 Hz, 1H), 2.90-2.70 (m, 2H), 2.18-1.96 (m, 1H), 1.93-1.44 (m, 3H); MS (ESI+) m/z 352.2 (M+H)+.

Aufarbeitung

  1. customquenched carefully with sat. NaHCO3
  2. customuntil bubbling
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. washthe combined organic extracts were washed with sat. NaHCO3, water and sat. NaCl
  5. dry with materialThe extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7791cce339b54963bbccac7d5a45681a
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889712B2

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