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Hydrochloric Acid → 2''-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylic acid

HRID 607068
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 607068
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=3[C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([O:42]C)=[O:41])=[CH:36][C:35]=4[CH3:44])[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[C@H:10]2[CH3:45])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[OH-].[K+].Cl.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[O:13][C:12](=[O:14])[N:11]([CH2:15][C:16]3[CH:21]=[C:20]([C:22]([F:23])([F:25])[F:24])[CH:19]=[CH:18][C:17]=3[C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([OH:42])=[O:41])=[CH:36][C:35]=4[CH3:44])[CH:29]=[CH:30][C:31]=3[O:32][CH3:33])[C@H:10]2[CH3:45])[CH:5]=[C:6]([Cl:8])[CH:7]=1
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Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 25010403methyl 2''-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

Produkt 1

HCID 25007959
2''-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4'-methoxy-2-methyl-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Methyl 2″-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate (EXAMPLE 26) (50 mg, 0.076 mmol), aqueous potassium hydroxide (600 μL, 3M, 1.8 mmol) and ethanol (4 mL) were stirred at 20° C. for 6 hours. The reaction mixture was acidified by HCl (aq., 1N) and then basified by sodium bicarbonate. Volatiles were removed under reduced pressure. The resulting mixture was worked up with ethyl acetate, washed with brine. The combined organic extracts were dried over Na2SO4, filtered, and concentrated to afford an oil. The oil was purified by preparative TLC (eluted with EtOAc/hexanes) to afford 2″-{[(4S,5R)-5-(3,5-dichlorophenyl)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]methyl}-4′-methoxy-2-methyl-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylic acid. LCMS calc.=643.11; found=644.14 (M+1)+. 1H NMR signals are doubled because of atropisomerism 1H NMR (CDCl3, 500 MHz) δ 8.01 (d, J=5.5 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.70 (s, 1H), 7.65-7.61 (m, 1.5H), 7.44-7.37 (m, 3H), 7.34-7.31 (m, 1H), 7.29 (d, J=8.0 Hz, 0.5H), 7.29 (d, J=8.0 Hz, 0.5H), 7.27-7.24 (m, 0.5H), 7.14 (dd, J=7.0, 2.5 Hz, 1H), 7.09-7.03 (m, 1.5H), 7.00 (dd, J=8.25, 2.0 Hz, 1H), 5.42 (d, J=8.5 Hz, 0.55H), 5.17 (d, J=8.0 Hz, 0.45H), 4.92 (d, J=16.0 Hz, 0.55H), 4.86 (d, J=16.0 Hz, 0.45H), 4.18 (d, J=15.5 Hz, 0.55H), 3.96 (d, J=15.5 Hz, 0.45H), 3.86 (s, 3H), 3.75-3.66 (m, 1H), 2.38, 2.34 (s, 3H), 0.56 (d, J=6.5 Hz; 1.35H), 0.44 (d, J=6.5 Hz, 1.65H).

Aufarbeitung

  1. customVolatiles were removed under reduced pressure
  2. washwashed with brine
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford an oil
  7. customThe oil was purified by preparative TLC (eluted with EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-3c34801231d34a018e90b532843b7ce4
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07915271B2

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