Benzyl 4-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)benzoate → 4-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)-benzoic Acid

HRID 735828

Reaktionsgleichung

Reaktionsgleichung von HRID 735828
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:36]=[CH:35][C:24]([C:25]([O:27]CC2C=CC=CC=2)=[O:26])=[CH:23][CH:22]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO>[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:35][CH:36]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 1

HCID 67186842Benzyl 4-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)benzoate

Produkt 1

HCID 671885994-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)-benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

H2 (1 atm) was bubbled slowly trough a suspension of 10% Pd/C (917 mg) in EtOH (25 mL) for 15 min at rt. To this suspension was then added a solution of benzyl 4-({(tert-butoxycarbonyl)[4-(trifluoromethyl)benzyl]amino}methyl)benzoate (4.303 g, 8.61 mmol) diluted in EtOH (5 mL). The resulting reaction mixture was stirred under 1 atm H2 for 4.5 h at rt. The reaction mixture was filtered over a pad of celite to remove the catalyst. EtOH was evaporated to afford the title compound as a colorless oil used in the next steps without further purification (3.520 g, 99%). 1H NMR (CDCl3, 300 MHz) δ 8.11 (d, J=8.1 Hz, 2H), 7.62 (d, J=8.1 Hz, 2H), 7.45-7.21 (m, 4H), 5.54 (s, 2H), 4.45 (s, 2H), 1.50 (s, 9H). HPLC (Condition A), Rt: 5.42 min (HPLC purity: 96.1%).

Aufarbeitung

  1. customH2 (1 atm) was bubbled slowly trough
  2. additiona suspension of 10% Pd/C (917 mg) in EtOH (25 mL) for 15 min at rt
  3. customThe resulting reaction mixture
  4. filtrationThe reaction mixture was filtered over a pad of celite
  5. customto remove the catalyst
  6. customEtOH was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f816f36cffc843c6ae46541ae267e55c
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592477B2

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