Hydrochloric Acid → 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid

HRID 505293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 505293
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][CH:36]=[O:37])[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(=CC)C.[O-:48]Cl=O.[Na+].Cl>C1COCC1.CC(O)(C)C.O.CCOC(C)=O>[F:42][C:2]([F:1])([F:41])[C:3]1[CH:4]=[C:5]([C@H:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([O:26][C:27]([F:28])([F:29])[F:30])[CH:23]=[CH:22][C:21]=3[N:31]([CH2:38][CH3:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:48])=[O:37])[C@H:14]2[CH3:40])[CH:6]=[C:7]([C:9]([F:11])([F:10])[F:12])[CH:8]=1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 248965325-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal

Produkt 1

HCID 248965335-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanal (6.8 mg, 0.011 mmol) in THF (20 μL) and t-BuOH (60 μL) was added 2-methyl-2-butene (20 μL), followed by a solution of NaClO2 (3.0 mg, 0.024 mmol) and NaH2PO4 (3.5 mg, 0.024 mmol) in water (25 μL). The reaction was stirred at room temperature for 30 minutes and then diluted with EtOAc (8 mL) and water (2 mL), acidified with 1 N HCl (2 mL), and washed with brine (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by PTLC (EtOAc) afforded 5-[[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl](ethyl)amino]pentanoic acid. Rf=0.20 (EtOAc). LCMS=631.3 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.88 (s, 1H), 7.78 (s, 2H), 7.18-7.15 (m, 3H), 5.73 (d, J=8.0 Hz, 1H), 4.75 (d, J=16.5 Hz, 1H), 4.58 (m, 1H), 4.03 (s, 1H), 2.97 (m, 4H), 2.31 (t, J=7.3 Hz, 2H), 1.40-1.23 (m, 5H), 1.00 (t, J=6.7 Hz, 3H), 0.69 (d, J=6.4 Hz, 3H).

Aufarbeitung

  1. washwashed with brine (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by PTLC (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bf61750d642742159ccdf7eb357c6cfd
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781426B2

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