Trifluoroacetic acid → (3R,4S)-1-Benzyl-4-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

HRID 1163342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1163342
[CH2:1]([O:3][C:4](=[O:25])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])=[CH:9][C:8]=1[F:24])[CH3:2].C(O[CH2:32][N:33]([CH2:41][Si](C)(C)C)[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)CCCC.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@@H:5]1[C@@H:6]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:15])=[CH:9][C:8]=2[F:24])[CH2:41][N:33]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:32]1)=[O:25])[CH3:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10902461N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamineHCID 672740363-(4-Benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic Acid Ethyl Ester

Produkt 1

HCID 68422745(3R,4S)-1-Benzyl-4-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-pyrrolidine-3-carboxylic Acid Ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4.5 g of 3-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-acrylic acid ethyl ester (13.1 mmol) and 7.68 g N-[(pentyloxy)methyl]-N-[(trimethylsilyl)-methyl]-benzenemethanamine (26.2 mmol) in 50 ml dichloromethane was added 10 μL. trifluoroacetic acid. The reaction was monitored by TLC. The reaction was complete after 10 min. The mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate solution and brine, dried over Mg sulfate, filtered and the filtrate evaporated. The residue was purified by filtration over a short silica column, using a 7/3 hexane/ethyl acetate mixture as eluent.

Aufarbeitung

  1. washwashed with sat. sodium bicarbonate solution and brine
  2. dry with materialdried over Mg sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated
  5. filtrationThe residue was purified by filtration over a short silica column

Quellen und Nachweise

ORD-Eintrag
ord-3d913782d1f343179d472c77816812c5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820823B2

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