Acetic Acid → HCID 58232113, Verbindung

HRID 2095585Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095585
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH:18]=[CH:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][C:23]([N:25]3[CH2:32][CH2:31][C:28]4([CH2:30][CH2:29]4)[C@H:27]([OH:33])[CH2:26]3)=[O:24])[CH2:14][C@H:13]2[CH3:34])[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].C(O)(=O)C>CO.O=[Pt]=O.O=[Pt]=O.[H][H]>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][C:23]([N:25]3[CH2:32][CH2:31][C:28]4([CH2:29][CH2:30]4)[C@H:27]([OH:33])[CH2:26]3)=[O:24])[CH2:14][C@H:13]2[CH3:34])[CH:5]=[CH:6][C:7]=1[C:8]([F:10])([F:9])[F:11]

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 58232178HCID 58232178, Verbindung

Produkt 1

HCID 58232113HCID 58232113, VerbindungAusbeute 113,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 345198Adams' catalystKatalysatorHCID 178506448HCID 178506448, VerbindungKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 0.066 g (0.1 mmol) of (R)-1-(3-chloro-4-trifluoromethyl-phenyl)-4-[4-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-4-oxo-butyl]-2-methyl-1,2,3,4-tetrahydro-[1,4]diazepin-5-one (61% ds) (example 65) in 2 ml MeOH was treated with 0.007 g of PtO2 and was stirred over H2-atmosphere for 2 days. After filtration and evaporation, the crude compound was again hydrogenated in 2 ml of MeOH and 0.007 ml (0.1 mmol) of acetic acid with 0.007 g of PtO2/H2 over night. After filtration and evaporation, the residue was reevaporated (3 times) with toluene and the solvent was removed under vacuum to give 0.057 g (86%) of the titled compound as white foam. MS: 502.21 (MH+, Cl).

Aufarbeitung

  1. filtrationAfter filtration and evaporation
  2. filtrationAfter filtration and evaporation
  3. customthe residue was reevaporated (3 times) with toluene
  4. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b98a333875e24bd5a6eadbc366057711
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445674B2

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