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Sodium borohydride → HCID 178471773, Verbindung

HRID 505310
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 505310
[NH2:1][C:2]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][C:3]=1[CH2:4][N:5]1[C@@H:9]([CH3:10])[C@@H:8]([C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=2)[O:7][C:6]1=[O:25].[CH:35]([C@H:37]1[CH2:42][CH2:41][C@H:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:39][CH2:38]1)=O.[BH4-].[Na+]>C1(C)C=CC=CC=1>[F:24][C:21]([F:22])([F:23])[C:13]1[CH:12]=[C:11]([C@H:8]2[O:7][C:6](=[O:25])[N:5]([CH2:4][C:3]3[CH:26]=[C:27]([O:30][C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:29][C:2]=3[NH:1][CH2:35][C@H:37]3[CH2:38][CH2:39][C@H:40]([CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])[CH2:41][CH2:42]3)[C@H:9]2[CH3:10])[CH:16]=[C:15]([C:17]([F:19])([F:20])[F:18])[CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 4311764Sodium borohydrideHCID 57617867(4S,5R)-3-[2-amino-5-(trifluoromethoxy)benzyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one2×HCID 178471795HCID 178471795, Verbindung2×

Produkt 1

HCID 178471773HCID 178471773, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140
Toluene
Lösungsmittel

Versuchsvorschrift

A stirred solution of (4S,5R)-3-[2-amino-5-(trifluoromethoxy)benzyl]-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (Intermediate 16; 820 mg; 1.63 mmol) and ethyl (trans-4-formylcyclohexyl)acetate (Intermediate 14; 270 mg; 1.36 mmol) in toluene (8 mL) was heated at reflux for 3 h. The reaction was concentrated in vacuo and redissolved in EtOH (8 mL). Sodium borohydride (103 mg; 2.72 mmol) was added and the reaction stirred at room temperature for 14 h. The reaction was quenched with sat. NH4Cl and partitioned between EtOAc (25 mL) and H2O (25 mL). The aqueous layer was re-extracted with EtOAc (3×25 mL) and the combined organic layers were washed with brine (25 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford ethyl [trans-4-({[2-({(4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-4-methyl-2-oxo-1,3-oxazolidin-3-yl}methyl)-4-(trifluoromethoxy)phenyl]amino}methyl)cyclohexyl]acetate as a yellow gum. LCMS=685.1 (M+1)+. 1H NMR (CDCl3, 500 MHz): δ 7.89 (s, 1 H), 7.73 (s, 2 H), 7.13 (d, J=8.7 Hz, 1 H), 6.92 (d, J=2.3 Hz, 1 H), 6.72 (d, J=9.0 Hz, 1 H), 5.66 (d, J=8.2 Hz, 1 H), 4.74 (d, J=15.6 Hz, 1 H), 4.14-4.02 (m, 4 H), 3.05-2.97 (m, 2 H), 2.19 (d, J=6.9 Hz, 2 H), 1.96-1.90 (m, 2 H), 1.85-1.78 (m, 2 H), 1.71-1.62 (m, 1 H), 1.51-1.39 (m, 2 H), 1.25 (t, J=7.1 Hz, 3 H), 1.12-1.03 (m, 3 H), 0.80 (d, J=6.4 Hz, 3 H).

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. concentrationThe reaction was concentrated in vacuo
  3. dissolutionredissolved in EtOH (8 mL)
  4. customThe reaction was quenched with sat. NH4Cl
  5. custompartitioned between EtOAc (25 mL) and H2O (25 mL)
  6. extractionThe aqueous layer was re-extracted with EtOAc (3×25 mL)
  7. washthe combined organic layers were washed with brine (25 mL)
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-1568f742666e472dbfd71a033822e864
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07781426B2

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