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(2R,5S)-2-(Acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester → (2S,5R)-5-(Acetylamino-methyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

HRID 1527352
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1527352
C(OC([N:11]1[C@H:15]([C:16](=[O:29])[NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=2)[CH2:14][CH2:13][C@@H:12]1[CH2:30][NH:31][C:32](=[O:34])[CH3:33])=O)C1C=CC=CC=1>C1COCC1.[Pd]>[F:27][C:25]([F:26])([F:28])[O:24][C:20]1[CH:19]=[C:18]([NH:17][C:16]([C@@H:15]2[CH2:14][CH2:13][C@H:12]([CH2:30][NH:31][C:32](=[O:34])[CH3:33])[NH:11]2)=[O:29])[CH:23]=[CH:22][CH:21]=1
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Komponenten

4

Edukt 1

HCID 68284355(2R,5S)-2-(Acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

Produkt 1

HCID 71042618(2S,5R)-5-(Acetylamino-methyl)-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2R,5S)-2-(acetylamino-methyl)-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (48 mg, 0.1 mmol) in THF (0.3 mL) was added Pd/C (10%, 2.1 mg). The solution was degassed 3 times replacing air by nitrogen and finally nitrogen by hydrogen. The reaction mixture was further stirred under hydrogen atmosphere for 5 h. The catalyst was removed through a pad of Celite and washed with THF. Solvents were concentrated and the resulting residue was used without further purification in the next step. MS (LC/MS): 346 [M+H]+; tR (HPLC conditions b): 2.94 min.

Aufarbeitung

  1. customThe solution was degassed 3 times
  2. customThe catalyst was removed through a pad of Celite
  3. washwashed with THF
  4. concentrationSolvents were concentrated
  5. customthe resulting residue was used without further purification in the next step
  6. custom2.94 min.

Quellen und Nachweise

ORD-Eintrag
ord-9a8387ceaf264c498ecb93035752e9bf
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09085555B2

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