Sodium methanesulfonate → (s)-2-[(s)-1-(4-Bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid [(s)-1-cyano-2-(4-methanesulfonyl-phenyl)-ethyl]-amide

HRID 239862

Reaktionsgleichung

Reaktionsgleichung von HRID 239862
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C@H:14]([C:19]([NH:21][C@H:22]([C:31]#[N:32])[CH2:23][C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[Na+].[CH3:34][S:35]([O-])(=[O:37])=[O:36]>CS(C)=O.CCOC(C)=O.[Cu](I)I>[C:31]([C@@H:22]([NH:21][C:19](=[O:20])[C@@H:14]([NH:13][C@@H:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[C:9]([F:12])([F:11])[F:10])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([S:35]([CH3:34])(=[O:37])=[O:36])=[CH:26][CH:25]=1)#[N:32]

Komponenten

6

Edukt 2

HCID 638112Sodium methanesulfonateHCID 68779205N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-L-leucinamide

Produkt 1

HCID 42633519(s)-2-[(s)-1-(4-Bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid [(s)-1-cyano-2-(4-methanesulfonyl-phenyl)-ethyl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To N2-[(1S)-1-(4-bromophenyl)-2,2,2-trifluoroethyl]-N-[(1S)-1-cyano-2-(4-iodophenyl)ethyl]-L-leucinamide (1 eq) in DMSO (0.3 M) were added methane sulfonic acid sodium salt (2 eq) and copper iodide (3 eq) and the mixture was stirred at 100° C. for 2 h. The reaction mixture was cooled and diluted with EtOAc. The organic layer was washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude compound was purified by automated SiO2 flash chromatography system using solvent gradient of 40% EtOAc/Hex to 100% EtOAc/Hex.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. washThe organic layer was washed with brine and water
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude compound was purified by automated SiO2 flash chromatography system

Quellen und Nachweise

ORD-Eintrag
ord-53f846116d2044d497afa95b5c656f0a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642799B2

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