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2,4-Dimethylbenzaldehyde → N-{(1S, 2S)-1-[(2,4-Dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-(2R/S)-2-methyl-N'-(3-trifluoromethyl-phenyl)-malonamide

HRID 1766844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1766844
C(O[C:9](=O)[NH:10][CH2:11][C@H:12]([NH:18][C:19](=[O:35])[CH:20]([C:22](=[O:34])[NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)[CH3:21])[C@@H:13]([OH:17])[C:14]#[C:15][CH3:16])C1C=CC=CC=1.[CH3:37][C:38]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:39]=1C=O.C([BH3-])#N.[Na+]>CO.[Pd]>[CH3:37][C:38]1[CH:45]=[C:44]([CH3:46])[CH:43]=[CH:42][C:39]=1[CH2:9][NH:10][CH2:11][C@H:12]([NH:18][C:19](=[O:35])[CH:20]([CH3:21])[C:22]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=1)=[O:34])[C@@H:13]([OH:17])[CH2:14][CH2:15][CH3:16]
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Komponenten

6

Edukt 3

HCID 618142,4-DimethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 69288737{(2S,3S)-3-hydroxy-2-[2-(3-trifluoromethyl-phenylcarbamoyl)-propionylamino]-hex-4-ynyl}-carbamic acid benzyl ester

Produkt 1

HCID 131726491N-{(1S, 2S)-1-[(2,4-Dimethyl-benzylamino)-methyl]-2-hydroxy-pentyl}-(2R/S)-2-methyl-N'-(3-trifluoromethyl-phenyl)-malonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938
Palladium
Katalysator
HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of {(2S,3S)-3-hydroxy-2-[2-(3-trifluoromethyl-phenylcarbamoyl)-propionylamino]-hex-4-ynyl}-carbamic acid benzyl ester (40 mg, 0.08 mmol) in MeOH (2 mL) was charged with 5% Pd/C, Degussa style (8 mg), stirred under H2 (1 atm) for 12 h at RT, filtered, and concentrated in vacuo. The residue was dissolved in MeOH (2 mL). The resultant solution was charged sequentially with 2,4-dimethylbenzaldehyde (0.009 mL, 0.06 mmol) and sodium cyanoborohydride (5 mg, 0.08 mmol), stirred for 12 h at RT, quenched with sat. NaHCO3, and extracted twice with EtOAc. The organic extracts were combined, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification of the residue by reverse-phase HPLC provided the title compound as a white powder after lyopholization. MS found: (M+H)+=494.4.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH (2 mL)
  4. stirringstirred for 12 h at RT
  5. customquenched with sat. NaHCO3
  6. extractionextracted twice with EtOAc
  7. washwashed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-40fce0cc769940e0b77d45e791440f2a
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07230133B2

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